Dropbox (DBX) 10-K 22 Feb 23 2022 FY Annual report Financial data

Cover Page

Cover Page - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Feb. 17, 2023	Jun. 30, 2022
Document Information [Line Items]
Document Type	10-K
Document Annual Report	true
Document Period End Date	Dec. 31, 2022
Current Fiscal Year End Date	--12-31
Document Transition Report	false
Entity File Number	001-38434
Entity Registrant Name	Dropbox, Inc.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	26-0138832
Entity Address, Address Line One	1800 Owens Street
Entity Address, City or Town	San Francisco
Entity Address, State or Province	CA
Entity Address, Postal Zip Code	94158
City Area Code	415
Local Phone Number	857-6800
Title of 12(b) Security	Class A Common Stock, par value $0.00001 per share
Trading Symbol	DBX
Security Exchange Name	NASDAQ
Entity Well-known Seasoned Issuer	Yes
Entity Voluntary Filers	No
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Large Accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	false
ICFR Auditor Attestation Flag	true
Entity Shell Company	false
Entity Public Float			$ 4,690.5
Documents Incorporated by Reference	Portions of the registrant's definitive Proxy Statement relating to the 2023 Annual Meeting of Stockholders are incorporated herein by references in Part II and Part III of this Annual Report on Form 10-K to the extent stated herein. Such Proxy Statement will be filed with the Securities and Exchange Commission within 120 days of the registrant's fiscal year ended December 31, 2022
Entity Central Index Key	0001467623
Document Fiscal Year Focus	2022
Document Fiscal Period Focus	FY
Amendment Flag	false
Class A Common Stock
Document Information [Line Items]
Entity Common Stock, Shares Outstanding		276,018,479
Class B Common Stock
Document Information [Line Items]
Entity Common Stock, Shares Outstanding		81,839,831
Class C Common Stock
Document Information [Line Items]
Entity Common Stock, Shares Outstanding		0

Audit Information

Audit Information	12 Months Ended
	Dec. 31, 2022
Audit Information [Abstract]
Auditor Firm ID	42
Auditor Name	Ernst & Young LLP
Auditor Location	San Francisco, California

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Current assets:
Cash and cash equivalents	$ 232.8	$ 533
Short-term investments	1,110.6	1,185.1
Trade and other receivables, net	53.8	49.6
Prepaid expenses and other current assets	92.6	82.1
Total current assets	1,489.8	1,849.8
Property and equipment, net	308.4	322
Operating lease right-of-use asset	260.6	413.9
Intangible assets, net	88.3	53.6
Goodwill	403.3	356.6
Deferred tax assets	498.7	41.2
Other assets	61	54.2
Total assets	3,110.1	3,091.3
Current liabilities:
Accounts payable	38.6	25.7
Accrued and other current liabilities	139.9	140.8
Accrued compensation and benefits	131.7	139.1
Operating lease liability	68.9	78.3
Finance lease obligation	114.8	120.4
Deferred revenue	702.6	671.5
Total current liabilities	1,196.5	1,175.8
Operating lease liability, non-current	585.2	632
Finance lease liability, non-current	151.7	167.7
Convertible senior notes, net, non-current	1,374	1,370.3
Other non-current liabilities	112.1	39.4
Total liabilities	3,419.5	3,385.2
Commitments and contingencies (Note 10)
Stockholders’ deficit:
Preferred stock value	0	0
Common stock	0	0
Additional paid-in capital	2,511.6	2,448.1
Accumulated deficit	(2,772.1)	(2,739.4)
Accumulated other comprehensive loss	(48.9)	(2.6)
Total stockholders’ deficit	(309.4)	(293.9)
Total liabilities and stockholders’ deficit	3,110.1	3,091.3
Convertible Preferred Stock
Stockholders’ deficit:
Preferred stock value	$ 0	$ 0

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - $ / shares	Dec. 31, 2022	Dec. 31, 2021
Preferred stock, par value (in dollars per share)	$ 0.00001	$ 0.00001
Preferred stock, shares authorized (in shares)	240,000,000	240,000,000
Preferred stock, shares issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Common stock, par value (in dollars per share)	$ 0.00001	$ 0.00001
Common stock, shares issued (in shares)		292,700,000
Convertible Preferred Stock
Preferred stock, par value (in dollars per share)	$ 0.00001	$ 0.00001
Preferred stock, shares authorized (in shares)	0	0
Preferred stock, shares issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Class A Common Stock
Common stock, par value (in dollars per share)	$ 0.00001
Common stock, shares authorized (in shares)	2,400,000,000	2,400,000,000
Common stock, shares issued (in shares)	267,200,000	292,700,000
Common stock, shares outstanding (in shares)	267,200,000	292,700,000
Class B Common Stock
Common stock, par value (in dollars per share)	$ 0.00001
Common stock, shares authorized (in shares)	475,000,000	475,000,000
Common stock, shares issued (in shares)	82,200,000	82,800,000
Common stock, shares outstanding (in shares)	82,200,000	82,800,000
Class C Common Stock
Common stock, par value (in dollars per share)	$ 0.00001
Common stock, shares authorized (in shares)	800,000,000	800,000,000
Common stock, shares issued (in shares)	0	0
Common stock, shares outstanding (in shares)	0	0

Consolidated Statements of Oper

Consolidated Statements of Operations - USD ($) shares in Millions, $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income Statement [Abstract]
Revenue		$ 2,324.9	$ 2,157.9	$ 1,913.9
Cost of revenue	[1]	444.2	444.2	414.6
Gross profit		1,880.7	1,713.7	1,499.3
Operating expenses
Research and development	[1]	891.9	755.9	727.5
Sales and marketing	[1]	409.4	427.5	422.8
General and administrative	[1]	222.9	224.6	227.8
Impairment related to real estate assets	[1],[2]	175.2	31.3	398.2
Total operating expenses		1,699.4	1,439.3	1,776.3
Income (loss) from operations		181.3	274.4	(277)
Interest income (expense), net		3.3	(5.2)	1.7
Other income, net		8.1	30.1	25.1
Income (loss) before income taxes		192.7	299.3	(250.2)
Benefit from (provision for) income taxes	[3]	360.5	36.5	(6.1)
Net income (loss)		$ 553.2	$ 335.8	$ (256.3)
Basic net income per share (in dollars per share)		$ 1.53	$ 0.87	$ (0.62)
Diluted net income per share (in dollars per share)		$ 1.52	$ 0.85	$ (0.62)
Weighted-average shares used in computing net income (loss) per share attributable to common stockholders, basic (in shares)		361.2	388	414.3
Weighted-average shares used in computing net income (loss) per share attributable to common stockholders, diluted (in shares)		363.3	395.8	414.3
[1]Includes stock-based compensation as follows (in millions): Year ended December 31, 2022 2021 2020 Cost of revenue $ 24.7 $ 23.2 $ 17.1 Research and development 232.3 190.1 174.1 Sales and marketing 22.4 25.0 33.7 General and administrative (4) 51.3 48.8 36.6

Consolidated Statements of Op_2

Consolidated Statements of Operations (Parenthetical) - USD ($) $ in Millions			12 Months Ended
		Mar. 19, 2020	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income tax benefit, release of deferred tax asset valuation allowance			$ 420.2	$ 38.1
Reversal of stock based compensation expense		$ 23.8
Reversal of stock based compensation expense previously recognized		$ 21.5
Cost of revenue
Allocated share-based compensation expense			24.7	23.2	$ 17.1
Research and development
Allocated share-based compensation expense			232.3	190.1	174.1
Sales and marketing
Allocated share-based compensation expense			22.4	25	33.7
General and administrative
Allocated share-based compensation expense	[1]		$ 51.3	$ 48.8	$ 36.6
[1]On March 19, 2020, one of the Company's co-founders resigned as a member of the board and as an officer of the Company, resulting in the reversal of $23.8 million in stock-based compensation expense. Of the total amount reversed, $21.5 million related to expense recognized prior to December 31, 2019.

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Income (Loss) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ 553.2	$ 335.8	$ (256.3)
Other comprehensive (loss) income, net of tax:
Change in foreign currency translation adjustments	(7.1)	(0.6)	4.8
Change in net unrealized (losses) gains on short-term investments	(39.2)	(12.9)	2.8
Total other comprehensive (loss) income, net of tax	(46.3)	(13.5)	7.6
Comprehensive income (loss)	$ 506.9	$ 322.3	$ (248.7)

Consolidated Statements of Stoc

Consolidated Statements of Stockholders' (Deficit) Equity - USD ($) $ in Millions	Total	Convertible preferred stock	Class A and Class B common stock	Additional paid-in capital	Accumulated deficit	Accumulated other comprehensive income (loss)
Shares outstanding, beginning balance (in shares) at Dec. 31, 2019		0
Shareholders equity, beginning balance at Dec. 31, 2019	$ 808.4	$ 0	$ 0	$ 2,531.3	$ (1,726.2)	$ 3.3
Shares outstanding, beginning balance (in shares) at Dec. 31, 2019			417,000,000
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Release of restricted stock units and awards (in shares)			13,100,000
Shares withheld related to net share settlement (in shares)			(4,700,000)
Shares withheld related to net share settlement	(92.2)			(43.5)	(48.7)
Repurchase of common stock (in shares)			(20,200,000)
Repurchases of common stock	(397.5)			(187.3)	(210.2)
Exercise of stock options and awards (in shares)			500,000
Exercise of stock options and awards	2.3			2.3
Stock-based compensation	261.5			261.5
Other comprehensive loss	7.6					7.6
Net loss	(256.3)				(256.3)
Shares outstanding, ending balance (in shares) at Dec. 31, 2020		0
Shareholders equity, ending balance at Dec. 31, 2020	$ 333.8	$ 0	$ 0	2,564.3	(2,241.4)	10.9
Shares outstanding, ending balance (in shares) at Dec. 31, 2020			405,700,000
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Release of restricted stock units and awards (in shares)			14,800,000
Shares withheld related to net share settlement (in shares)	(4,600,000)		(4,600,000)
Shares withheld related to net share settlement	$ (124.8)			(35.2)	(89.6)
Repurchase of common stock (in shares)			(41,100,000)
Repurchases of common stock	$ (1,058.5)			(314.3)	(744.2)
Exercise of stock options and awards (in shares)	700,000		700,000
Exercise of stock options and awards	$ 6.9			6.9
Assumed stock options in connection with acquisition	1.2			1.2
Purchase of bond hedges in connection with issuance of convertible senior notes	(265.3)			(265.3)
Sale of warrants in connection with issuance of convertible senior notes	202.9			202.9
Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes	0.5			0.5
Stock-based compensation	287.1			287.1
Other comprehensive loss	(13.5)					(13.5)
Net loss	$ 335.8				335.8
Shares outstanding, ending balance (in shares) at Dec. 31, 2021	0	0
Shareholders equity, ending balance at Dec. 31, 2021	$ (293.9)	$ 0	$ 0	2,448.1	(2,739.4)	(2.6)
Shares outstanding, ending balance (in shares) at Dec. 31, 2021			375,500,000
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Release of restricted stock units and awards (in shares)			14,400,000
Shares withheld related to net share settlement (in shares)	(5,100,000)		(5,100,000)
Shares withheld related to net share settlement	$ (119.4)			(41.5)	(77.9)
Repurchase of common stock (in shares)			(35,600,000)
Repurchases of common stock	$ (795.4)			(287.4)	(508)
Exercise of stock options and awards (in shares)	100,000		200,000
Exercise of stock options and awards	$ 0.5			0.5
Tax benefit attributable to bond hedges purchased in connection with issuance of convertible senior notes	61.2			61.2
Stock-based compensation	330.7			330.7
Other comprehensive loss	(46.3)					(46.3)
Net loss	$ 553.2				553.2
Shares outstanding, ending balance (in shares) at Dec. 31, 2022	0	0
Shareholders equity, ending balance at Dec. 31, 2022	$ (309.4)	$ 0	$ 0	$ 2,511.6	$ (2,772.1)	$ (48.9)
Shares outstanding, ending balance (in shares) at Dec. 31, 2022			349,400,000

Consolidated Statements of Cash

Consolidated Statements of Cash Flows - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Cash flows from operating activities
Net income (loss)		$ 553.2	$ 335.8	$ (256.3)
Adjustments to reconcile net loss to net cash provided by operating activities:
Depreciation and amortization		157.1	151.4	159.3
Stock-based compensation		330.7	287.1	261.5
Impairment related to real estate assets	[1],[2]	175.2	31.3	398.2
Amortization of debt issuance costs		4.2	3.8	0.6
Net gains on equity investments		(5)	0	(17.5)
Amortization of deferred commissions		39.5	32.3	24.4
Net gains on lease termination		0	(13.6)	0
Non-cash operating lease expense		63.8	76.3	81.1
Deferred taxes		(396.3)	(37.5)	(2.5)
Other		(0.8)	(4.4)	(2.6)
Changes in operating assets and liabilities:
Trade and other receivables, net		(5.5)	(6.2)	(5.5)
Prepaid expenses and other current assets		(50)	(58.4)	(39.4)
Other assets		(9.7)	11.7	(17.2)
Accounts payable		13	7.6	(19.9)
Accrued and other current liabilities		4.7	(28.6)	(9.3)
Accrued compensation and benefits		(6.8)	23.5	11.7
Deferred revenue		25.6	59.8	55.1
Other non-current liabilities		(17.9)	(13.1)	4
Operating lease liabilities		(86.4)	(102.1)	(77.4)
Tenant improvement allowance reimbursement		8.7	5.1	22.5
Cash paid for lease termination		0	(32)	0
Net cash provided by operating activities		797.3	729.8	570.8
Cash flows from investing activities
Capital expenditures		(33.8)	(22.1)	(80.1)
Purchase of intangible assets		(1.1)	(6.8)	(0.2)
Business combinations, net of cash acquired		(75.4)	(140)	0
Purchases of short-term investments		(571.2)	(1,138.4)	(756.1)
Proceeds from sales of short-term investments		213.7	293.6	172.4
Proceeds from maturities of short-term investments		389.1	448.7	386.7
Proceeds from sales of equity investments		10.6	0	26.4
Other		19.6	40.2	17.3
Net cash used in investing activities		(48.5)	(524.8)	(233.6)
Cash flows from financing activities
Proceeds from issuance of convertible senior notes		0	1,389.1	0
Purchases of convertible note hedge in connection with issuance of convertible senior notes		0	(265.3)	0
Proceeds from sale of warrants in connection with issuance of convertible senior notes		0	202.9	0
Payments of debt issuance costs		0	(23.7)	0
Payments for taxes related to net share settlement of restricted stock units and awards		(119.4)	(124.8)	(92.2)
Proceeds from issuance of common stock, net of taxes withheld		0.5	6.9	2.3
Principal payments on finance lease obligations		(127.5)	(110.4)	(89.5)
Common stock repurchases		(795.4)	(1,058.5)	(397.5)
Other		0	0	(0.8)
Net cash (used in) provided by financing activities		(1,041.8)	16.2	(577.7)
Effect of exchange rate changes on cash and cash equivalents		(7.2)	(3.1)	4.1
Change in cash and cash equivalents		(300.2)	218.1	(236.4)
Cash and cash equivalents—beginning of period		533	314.9	551.3
Cash and cash equivalents—end of period		232.8	533	314.9
Supplemental cash flow data:
Interest		8.2	8.5	9.6
Income taxes		27.6	4.2	5
Non-cash investing and financing activities:
Property and equipment received and accrued in accounts payable and accrued liabilities		2.6	5.6	7.8
Property and equipment acquired under finance leases		$ 105.8	$ 127.3	$ 145.8
[1]Includes impairment charges related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted the Company's subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information.[2]Includes stock-based compensation as follows (in millions): Year ended December 31, 2022 2021 2020 Cost of revenue $ 24.7 $ 23.2 $ 17.1 Research and development 232.3 190.1 174.1 Sales and marketing 22.4 25.0 33.7 General and administrative (4) 51.3 48.8 36.6

Description of the Business and

Description of the Business and Summary of Significant Accounting Policies	12 Months Ended
	Dec. 31, 2022
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Description of the Business and Summary of Significant Accounting Policies	Description of the Business and Summary of Significant Accounting Policies Business Dropbox, Inc. (the “Company” or “Dropbox”) helps keep life organized and work moving. The Company was incorporated in May 2007 as Evenflow, Inc., a Delaware corporation, and changed its name to Dropbox, Inc. in October 2009. The Company is headquartered in San Francisco, California. Basis of presentation and consolidation The accompanying consolidated financial statements have been prepared in accordance with the United States of America generally accepted accounting principles (“GAAP”). The accompanying consolidated financial statements include the accounts of Dropbox and its wholly owned subsidiaries. All intercompany balances and transactions have been eliminated in consolidation. Use of estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported and disclosed in the Company’s consolidated financial statements and accompanying notes. These estimates are based on information available as of the date of the consolidated financial statements. Management evaluates these estimates and assumptions on a regular basis. Actual results may differ materially from these estimates. The Company’s most significant estimates and judgments involve the valuation of right-of-use and other lease related assets and income taxes. Financial information about segments and geographic areas The Company manages its operations and allocates resources as a single operating segment. Further, the Company manages, monitors, and reports its financials as a single reporting segment. The Company’s chief operating decision-maker is its Chief Executive Officer, who reviews financial information presented on a consolidated basis for purposes of making operating decisions, assessing financial performance, and allocating resources. See Note 15, "Geographic Areas" for information regarding the Company’s long-lived assets and revenue by geography. Foreign currency transactions The assets and liabilities of the Company’s foreign subsidiaries are translated from their respective functional currencies into U.S. dollars at the exchange rates in effect at the balance sheet date. Revenue and expense amounts are translated at the average exchange rate for the period. Foreign currency translation gains and losses are recorded in other comprehensive (loss) income, net of tax. Gains and losses realized from foreign currency transactions (those transactions denominated in currencies other than the foreign subsidiaries’ functional currency) are included in other income, net. Monetary assets and liabilities are remeasured using foreign currency exchange rates at the end of the period, and non-monetary assets are remeasured based on historical exchange rates. The Company recorded net foreign currency transaction gains of $0.2 million and losses of $1.8 million in the years ended December 31, 2022 and 2021, respectively. Revenue recognition The Company derives its revenue from subscription fees from customers for access to its platform. The Company’s policy is to exclude sales and other indirect taxes when measuring the transaction price of its subscription agreements. The Company accounts for revenue contracts with customers through the following steps: • Identification of the contract, or contracts, with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract • Recognition of revenue when, or as, the Company satisfies a performance obligation The Company’s subscription agreements generally have monthly or annual contractual terms and a small percentage have multi-year contractual terms. Revenue is recognized ratably over the related contractual term beginning on the date that the platform is made available to a customer. Access to the platform represents a series of distinct services as the Company continually provides access to, and fulfills its obligation to, the end customer over the subscription term. The series of distinct services represents a single performance obligation that is satisfied over time. The Company recognizes revenue ratably because the customer receives and consumes the benefits of the platform throughout the contract period. The Company’s contracts are generally non-cancelable. The Company bills in advance for monthly contracts and typically bills annually in advance for contracts with terms of one year or longer. The Company also recognizes an immaterial amount of contract assets, or unbilled receivables, primarily relating to consideration for services completed but not billed at the reporting date. Unbilled receivables are classified as receivables when the Company has the right to invoice the customer. The Company records contract liabilities when cash payments are received or due in advance of performance to deferred revenue. Deferred revenue primarily relates to the advance consideration received from the customer. The price of subscriptions is generally fixed at contract inception and therefore, the Company’s contracts do not contain a significant amount of variable consideration. As a result, the amount of revenue recognized in the periods presented from performance obligations satisfied (or partially satisfied) in previous periods was not material. The Company recognized $671.5 million, $610.5 million, and $554.2 million of revenue during the years ended December 31, 2022, 2021, and 2020 respectively, that was included in the deferred revenue balances at the beginning of their respective periods. As of December 31, 2022, future estimated revenue related to performance obligations that were unsatisfied or partially unsatisfied was $774.2 million. The substantial majority of the unsatisfied performance obligations will be satisfied over the next twelve months. Stock-based compensation The Company has primarily granted restricted stock units (“RSUs”) to its employees and members of the Board of Directors under the 2008 Equity Incentive Plan (“2008 Plan”), the 2017 Equity Incentive Plan (“2017 Plan”), and the 2018 Equity Incentive Plan (“2018 Plan” and together with the 2008 Plan and 2017 Plan, the "Dropbox Equity Incentive Plans”). Since August 2015, the Company has granted RSUs, which have a service based vesting condition over a four-year period vesting quarterly, as the only stock-based payment awards to its employees, with the exception of awards granted to its co-founder and certain executives, and has not granted any stock options to employees under the Dropbox Equity Incentive Plans. The Company recognizes compensation expense associated with RSUs on a straight-line basis over the requisite service period and accounts for forfeitures in the period in which they occur. The Board of Directors determines the fair value of each share of underlying common stock based on the closing price of the Company's Class A common stock as reported on the Nasdaq Global Select Market on the date of the grant. In March 2021, in connection with the acquisition of DocSend, Inc. (“DocSend”), the Company assumed unvested stock options and an immaterial number of unvested RSUs that had been granted under DocSend's 2013 Stock Plan and DocSend's 2015 Stock Option and Grant Plan. The fair value of the DocSend options assumed were based upon the Black-Scholes option-pricing model. See Note 12 "Stockholders' (Deficit) Equity" for further information. In December 2017, the Board of Directors approved the Company’s Co-Founder Grant, consisting of 10.3 million shares of Class A Common Stock in the form of restricted stock awards ("RSAs") which were granted to Drew Houston, the Company’s co-founder and Chief Executive Officer. This Co-Founder Grant has service-based, market-based, and performance-based vesting conditions. The Co-Founder Grant is excluded from Class A common stock issued and outstanding until the satisfaction of these vesting conditions. The Company estimated the grant date fair value of the Co-Founder Grant using a model based on multiple stock price paths developed through the use of a Monte Carlo simulation that incorporates into the valuation the possibility that the certain stock price targets may not be satisfied. The first tranche of the Co-Founder Grant vested in the fourth quarter of 2021. The stock-based compensation expense for the Co-Founder Grant is recognized utilizing the accelerated attribution method over the requisite service period identified as the derived service period over which the market conditions are expected to be achieved, and is not reversed if the market conditions are not satisfied. Therefore, no incremental stock-based compensation was recognized upon vesting of these RSAs. See Note 12, "Stockholders' (Deficit) Equity" for further information. Cost of revenue Cost of revenue consists primarily of expenses associated with the storage, delivery, and distribution of the Company’s platform for both paying users and free users. These costs, which are referred to as infrastructure costs, include depreciation of servers located in co-location facilities that the Company leases and operates, rent and facilities expense for those datacenters, network and bandwidth costs, support and maintenance costs for infrastructure equipment, and payments to third-party datacenter service providers. Cost of revenue also includes costs, such as salaries, bonuses, benefits, travel-related expenses, and stock-based compensation, which are referred to as employee-related costs, for employees whose primary responsibilities relate to supporting the Company’s infrastructure and delivering user support. Other non-employee costs included in cost of revenue include credit card fees related to processing customer transactions and allocated overhead, such as facilities, including rent, utilities, depreciation on leasehold improvements and other equipment shared by all departments, and shared information technology costs. In addition, cost of revenue includes amortization of developed technologies, professional fees related to user support initiatives, and property taxes related to the datacenters. Advertising and promotional expense Advertising and promotional expenses are primarily included in sales and marketing expenses within the consolidated statements of operations and are expensed when incurred. Advertising and promotional expenses were $94.8 million, $108.6 million, and $81.4 million during the years ended December 31, 2022, 2021, and 2020, respectively. Cash and cash equivalents Cash consists primarily of cash on deposit with banks and includes amounts in transit from payment processors for credit and debit card transactions, which typically settle within five business days. Cash equivalents include highly liquid investments purchased with an original maturity date of 90 days or less from the date of purchase. The Company monitors its credit risk by considering factors such as historical experience, credit ratings, current economic conditions, and reasonable and supportable forecasts. Short-term investments The Company’s short-term investments are primarily comprised of corporate notes and obligations, U.S. Treasury securities, certificates of deposit, asset-backed securities, commercial paper, U.S. agency obligations, foreign government securities, supranational securities, and municipal securities. The Company determines the appropriate classification of its short-term investments at the time of purchase and reevaluates such designation at each balance sheet date. The Company has classified and accounted for its short-term investments as available-for-sale securities as the Company may sell these securities at any time for use in its current operations or for other purposes, even prior to maturity. As a result, the Company classifies its short-term investments, including securities with stated maturities beyond twelve months, within current assets in the consolidated balance sheets. The Company's short-term investments are recorded at fair value each reporting period. Unrealized gains and losses on these short-term investments are reported as a separate component of accumulated other comprehensive loss in the consolidated balance sheets until realized. Unrealized gains and losses for any short-term investments that management intends to sell or it is more likely than not that management will be required to sell prior to their anticipated recovery are recorded in other income, net. The Company segments its portfolio based on the underlying risk profiles of the securities and has a zero-loss expectation for U.S. treasury and U.S. government agency securities. The Company regularly reviews the securities in an unrealized loss position and evaluates the current expected credit loss by considering factors such as credit ratings, issuer-specific factors, current economic conditions, and reasonable and supportable forecasts. The Company did not record any material credit losses during the year ended December 31, 2022. Concentrations of credit risk Financial instruments that potentially subject the Company to significant concentrations of credit risk consist primarily of cash, cash equivalents, accounts receivable, and short-term investments. The Company places its cash and cash equivalents, and short-term investments with well-established financial institutions. Trade accounts receivable are typically unsecured and are derived from revenue earned from customers located around the world. Two distribution partners accounted for 12% and 30% of total trade and other receivables, net as of December 31, 2022. Two distribution partners accounted for 14% and 29% of total trade and other receivables, net as of December 31, 2021. No customer accounted for more than 10% of the Company’s revenue in the periods presented. Trade and other receivables, net Trade and other receivables, net consists primarily of trade receivables that are recorded at the invoice amount, net of an allowance for expected credit losses. The allowance for expected credit losses is based on the Company’s assessment of the collectability of accounts receivable. The Company assesses collectability by reviewing accounts receivable on a collective basis where similar characteristics exist and on an individual basis when the Company identifies specific customers with known disputes or collectability issues. The Company regularly reviews the adequacy of the allowance for expected credit losses by considering the age of each outstanding invoice, the collection history of each customer, and other relevant factors, including contractual term and current and future economic conditions. The Company's allowance for expected credit losses was $0.7 million and $1.0 million as of December 31, 2022 and 2021, respectively. Non-trade receivables The Company records non-trade receivables to reflect amounts due for activities outside of its subscription agreements, such as indemnification assets and receivables from tenants. Non-trade receivables totaled $6.5 million and $4.1 million, as of December 31, 2022 and 2021, respectively, and are classified within prepaid expenses and other current assets in the accompanying consolidated balance sheets. See "—Lease obligations” for further discussion. Deferred commissions, net Deferred commissions, net is stated as gross deferred commissions less accumulated amortization. Sales commissions earned by the Company’s sales force and third-party resellers, as well as related payroll taxes, are considered to be incremental and recoverable costs of obtaining a contract with a customer. These amounts have been capitalized as deferred commissions within prepaid and other current assets and other assets on the consolidated balance sheets. The Company deferred incremental costs of obtaining a contract of $33.5 million and $23.7 million during the years ended December 31, 2022 and 2021, respectively. Deferred commissions, net included in prepaid and other current assets were $33.6 million and $30.8 million as of December 31, 2022 and 2021, respectively. Deferred commissions, net included in other assets were $25.7 million and $34.6 million as of December 31, 2022 and 2021, respectively. Commissions related to new contracts are typically deferred and amortized over a period of benefit of five years. The period of benefit was estimated by considering factors such as historical customer attrition rates, the useful life of the Company’s technology, and the impact of competition in its industry. Commissions that are commensurate with renewal contracts are typically amortized over one year. Amortization of deferred commissions costs was $39.5 million, $32.3 million, and $24.4 million for the years ended December 31, 2022, 2021, and 2020, respectively. Amortization of deferred commissions costs are included in sales and marketing expense in the accompanying consolidated statements of operations. There was no material impairment loss in relation to the deferred costs for any period presented. Property and equipment, net Equipment is stated at cost less accumulated depreciation. Depreciation is computed using the straight-line method over the estimated useful life of the related asset, which is generally three The following table presents the estimated useful lives of property and equipment: Property and equipment Useful life Buildings 20 to 30 years Datacenter and other computer equipment 3 to 5 years Office equipment and other 3 to 7 years Leasehold improvements Lesser of estimated useful life or remaining lease term Lease obligations The Company leases office space, datacenters, and equipment under non-cancelable finance and operating leases with various expiration dates through 2036. The Company determines if an arrangement contains a lease at inception. Operating lease right-of-use assets and lease liabilities are recognized at the present value of the future lease payments at commencement date. The interest rate implicit in the Company’s operating leases is not readily determinable, and therefore an incremental borrowing rate is estimated to determine the present value of future payments. The estimated incremental borrowing rate factors in a hypothetical interest rate on a collateralized basis with similar terms, payments, and economic environments. Operating lease right-of-use assets also include any prepaid lease payments and lease incentives. Certain of the operating lease agreements contain rent concession, rent escalation, and option to renew provisions. Rent concession and rent escalation provisions are considered in determining the single lease cost to be recorded over the lease term. Single lease cost is recognized on a straight-line basis over the lease term commencing on the date the Company has the right to use the leased property. The lease terms may include options to extend or terminate the lease. The Company generally uses the base, non-cancelable, lease term when recognizing the lease assets and liabilities, unless it is reasonably certain that the option will be exercised. In addition, certain operating lease agreements contain tenant improvement allowances from its landlords. These allowances are accounted for as lease incentives and decrease the Company's right-of-use asset and reduce single lease cost over the lease term. As part of the Company's Virtual First strategy, Dropbox has retained a portion of its office space for in-person collaboration while the remainder will be subleased. During the year ended December 31, 2022, the Company recorded impairment charges of $175.2 million related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted its subleasing strategy in conjunction with its shift to Virtual First. During the year ended December 31, 2021, the Company recorded an impairment charge of $31.3 million related to its operating leases and related real estate assets, and assets acquired as part of the acquisition of DocSend in the first quarter of 2021. These impairment charges were recorded as a result of adverse changes in the corporate real estate market which impacted its subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information. The Company leases certain equipment from various third parties, through equipment finance leases. These leases either include a bargain purchase option, a full transfer of ownership at the completion of the lease term, or the terms of the leases are at least 75 percent of the useful lives of the assets and are therefore classified as finance leases. These leases are capitalized in property and equipment, net and the related amortization of assets under finance leases is included in depreciation and amortization expense in the Company’s consolidated statements of operations. Initial asset values and finance lease obligations are based on the present value of future minimum lease payments. The Company’s finance lease agreements may contain lease and non-lease components. The non-lease components include payments for support on infrastructure equipment obtained via finance leases, which when not significant in relation to the overall agreement, are combined with the lease components and accounted for together as a single lease component. Internal use software The Company capitalizes certain costs related to developed or modified software solely for its internal use and cloud based applications used to deliver its platform. The Company capitalizes costs during the application development stage once the preliminary project stage is complete, management authorizes and commits to funding the project, and it is probable that the project will be completed and that the software will be used to perform the function intended. Costs related to preliminary project activities and post implementation activities are expensed as incurred. Capitalized internal use software costs were not material to the Company’s consolidated financial statements during the years ended December 31, 2022, 2021, and 2020. Business combinations The Company uses best estimates and assumptions, including but not limited to, future expected cash flows, expected asset lives, and discount rates, to assign a fair value to the tangible and intangible assets acquired and liabilities assumed in business combinations as of the acquisition date. These estimates are inherently uncertain and subject to refinement. During the measurement period, which may be up to one year from the acquisition date, adjustments to the fair value of these tangible and intangible assets acquired and liabilities assumed may be recorded, with the corresponding offset to goodwill. Upon the conclusion of the measurement period or final determination of the fair value of assets acquired or liabilities assumed, whichever comes first, any subsequent adjustments are recorded to the Company’s consolidated statements of operations. Long-lived assets, including goodwill and other acquired intangible assets, net The Company evaluates the recoverability of its property and equipment and finite-lived intangible assets for possible impairment whenever events or circumstances indicate that the carrying amount of such assets may not be recoverable. The evaluation is performed at the lowest level for which identifiable cash flows are largely independent of the cash flows of other assets and liabilities. Recoverability of these assets is measured by a comparison of the carrying amounts to the future undiscounted cash flows the assets are expected to generate. If such review determines that the carrying amount of specific property and equipment or intangible assets is not recoverable, the carrying amount of such assets is reduced to its fair value. The Company reviews goodwill for impairment at least annually in the fourth quarter, or more frequently if events or changes in circumstances would more likely than not reduce the fair value of its single reporting unit below its carrying value. At December 31, 2022, the single reporting unit had a zero or negative carrying value of net assets. Goodwill allocated to the single reporting unit is $403.3 million at December 31, 2022. The Company has not recorded impairment charges on goodwill or intangible assets for the periods presented in these consolidated financial statements. The Company recorded impairment charges of $175.2 million and $31.3 million related to real estate assets and other lease related obligations during the years ended December 31, 2022 and 2021, respectively, in conjunction with its decision to move towards a Virtual First work model. See Note 9 "Leases" for further information. Acquired property and equipment and finite-lived intangible assets are amortized over their useful lives. The Company evaluates the estimated remaining useful life of these assets when events or changes in circumstances warrant a revision to the remaining period of amortization. If the Company revises the estimated useful life assumption for any asset, the remaining unamortized balance is amortized or depreciated over the revised estimated useful life on a prospective basis. Income taxes Deferred income tax balances reflect the effects of temporary differences between the financial reporting and tax bases of the Company’s assets and liabilities using enacted tax rates expected to apply when taxes are actually paid or recovered. In addition, deferred tax assets are recorded for net operating loss and credit carryforwards. A valuation allowance is provided against deferred tax assets unless it is more likely than not that they will be realized based on all available positive and negative evidence. Such evidence includes, but is not limited to, recent cumulative earnings or losses, expectations of future taxable income by taxing jurisdiction, and the carry-forward periods available for the utilization of deferred tax assets. As of December 31, 2022, the Company determined that all of its deferred tax assets related to federal and certain states are more likely than not to be realized, resulting in a benefit to income taxes of $420.2 million from the release of the valuation allowance. As of December 31, 2021, the Company released the valuation allowance on its Irish deferred tax assets resulting in an income tax benefit of $38.1 million. The Company uses a two-step approach to recognizing and measuring uncertain income tax positions. The first step is to evaluate the tax position for recognition by determining if the weight of available evidence indicates it is more likely than not that the position will be sustained on audit. The second step is to measure the tax benefit as the largest amount, which is more than 50% likely of being realized upon ultimate settlement. The Company recognizes interest and penalties related to unrecognized tax benefits as income tax expense. Although the Company believes that it has adequately reserved for its uncertain tax positions, it can provide no assurance that the final tax outcome of these matters will not be materially different. The Company evaluates its uncertain tax positions on a regular basis and evaluations are based on a number of factors, including changes in facts and circumstances, changes in tax law, correspondence with tax authorities during the course of an audit, and effective settlement of audit issues. To the extent that the final tax outcome of these matters is different than the amounts recorded, such differences will affect the provision for income taxes in the period in which such determination is made and could have a material impact on the Company’s financial condition and results of operations. The Tax Cuts and Jobs Act of 2017 ("TCJA") subjects a U.S. shareholder to current tax global intangible low-taxed income ("GILTI") earned by foreign subsidiaries. We account for GILTI as a period cost as incurred. Fair value measurement The Company applies fair value accounting for all financial assets and liabilities and non-financial assets and liabilities that are recognized or disclosed at fair value in the financial statements on a recurring basis. The Company defines fair value as the price that would be received from selling an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. When determining fair value measurements for assets and liabilities, the Company considers the principal or most advantageous market in which it would transact and the market-based risk measurements or assumptions that market participants would use in pricing the asset or liability, such as risks inherent in valuation techniques, transfer restrictions, and credit risk. Fair value is estimated by applying the following hierarchy, which prioritizes the inputs used to measure fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available and significant to the fair value measurement: Level 1 —Quoted prices in active markets for identical assets or liabilities. Level 2 —Observable inputs other than quoted prices in active markets for identical assets and liabilities, quoted prices for identical or similar assets or liabilities in inactive markets, or other inputs that are observable or can be corroborated by observable market data for substantially the full term of the assets or liabilities. Level 3 —Inputs that are generally unobservable and typically reflect management’s estimate of assumptions that market participants would use in pricing the asset or liability. Recently issued accounting pronouncements not yet adopted In March 2022, the FASB issued ASU 2022-02, Financial Instruments—Credit Losses (Topic 326): Troubled Debt Restructurings and Vintage Disclosures , which eliminates the accounting guidance on troubled debt restructurings for creditors in ASC 310-40 and amends the guidance on "vintage disclosures" to require disclosure of current-period gross write-offs by year of origination. The ASU also updates the requirements related to accounting for credit losses under ASC 326 and adds enhanced disclosures for creditors with respect to loan refinancings and restructurings for borrowers experiencing financial difficulty. The amendments in ASU 2022-02 are effective for fiscal years beginning after December 15, 2022, and interim periods within those fiscal years. The Company does not expect the adoption of ASU 2022-02 to have a significant impact on its consolidated financial statements. Recently adopted accounting pronouncements In May 2021, the FASB issued ASU 2021-04, Earnings Per Share (Topic 260), Debt - Modifications and Extinguishments (Subtopic 470-50), Compensation - Stock Compensation (Topic 718), and Derivatives and Hedging - Contracts in Entity's Own Equity (Subtopic 815-40) to clarify and reduce diversity in an issuer’s accounting for modifications or exchanges of freestanding equity-classified written call options (for example, warrants) that remain equity classified after modification or exchange. The Company adopted ASU 2021-04 on January 1, 2022. The adoption of the standard did not have a material impact on the Company's consolidated financial statements. In July 2021, the FASB issued ASU 2021-05, Leases (Topic 842) , which amends ASC 842 so that lessors are no longer required to recognize a selling loss upon commencement of a lease with variable lease payments that, prior to the amendments, would have been classified as a sales-type or direct financing lease. Furthermore, a lessor must classify as an operating lease any lease that would otherwise be classified as a sales-type or direct financing lease and that would result in the recognition of a selling loss at lease commencement, provided that the lease includes variable lease payments that do not depend on an index or rate. The Company adopted ASU 2021-05 on January 1, 2022. The adoption of the standard did not have a material impact on the Company's consolidated financial statements. In October 2021, the FASB issued ASU 2021-08, Business Combinations (Topic 805): Accounting for Contract Assets and Contract Liabilities from Contracts with Customers , which requires entities to recognize and measure contract assets and contract liabilities acquired in a business combination in accordance with Topic 606, Revenue from Contracts with Customers, instead of fair value at the acquisition date in accordance with Topic 805. The amendments in ASU 2021-08 results in the acquirer recording acquired contract assets and liabilities on

Cash, Cash Equivalents and Shor

Cash, Cash Equivalents and Short-Term Investments	12 Months Ended
	Dec. 31, 2022
Cash and Cash Equivalents [Abstract]
Cash, Cash Equivalents and Short-Term Investments	Cash, Cash Equivalents and Short-Term Investments The amortized cost, unrealized gains and losses and estimated fair value of the Company's cash, cash equivalents and short-term investments as of December 31, 2022 consisted of the following: Amortized cost Unrealized gain Unrealized loss Estimated fair value Cash $ 90.1 $ — $ — $ 90.1 Cash equivalents Money market funds 139.5 — — 139.5 Commercial paper 3.2 — — 3.2 Total cash & cash equivalents $ 232.8 $ — $ — $ 232.8 Short-term investments Corporate notes and obligations 512.1 0.1 (22.7) 489.5 U.S. Treasury securities 360.2 0.2 (14.0) 346.4 Asset backed securities 117.6 — (6.0) 111.6 Municipal securities 65.3 — (4.1) 61.2 Commercial paper 46.4 — — 46.4 Certificates of deposit 29.1 — — 29.1 U.S. agency obligations 18.4 — (0.8) 17.6 Foreign government obligations 6.0 — (0.4) 5.6 Supranational securities 3.4 — (0.2) 3.2 Total short-term investments 1,158.5 0.3 (48.2) 1,110.6 Total $ 1,391.3 $ 0.3 $ (48.2) $ 1,343.4 The amortized cost, unrealized gains and losses and estimated fair value of the Company's cash, cash equivalents and short-term investments as of December 31, 2021 consisted of the following: Amortized cost Unrealized gain Unrealized loss Estimated fair value Cash $ 142.7 $ — $ — $ 142.7 Cash equivalents Money market funds 390.3 — — 390.3 Total cash and cash equivalents $ 533.0 $ — $ — $ 533.0 Short-term investments Corporate notes and obligations 607.4 0.4 (4.0) 603.8 U.S. Treasury securities 240.4 — (2.9) 237.5 Asset backed securities 140.7 0.1 (1.2) 139.6 Municipal securities 70.5 — (0.7) 69.8 U.S. agency obligations 14.6 — (0.2) 14.4 Commercial paper 61.7 — — 61.7 Supranational Securities 8.0 — (0.1) 7.9 Foreign government obligations 18.4 — (0.1) 18.3 Certificates of deposit 32.1 — — 32.1 Total short-term investments 1,193.8 0.5 (9.2) 1,185.1 Total $ 1,726.8 $ 0.5 $ (9.2) $ 1,718.1 Included in cash and cash equivalents is cash in transit from payment processors for credit and debit card transactions of $12.4 million and $8.3 million as of December 31, 2022 and December 31, 2021, respectively. All short-term investments were designated as available-for-sale securities as of December 31, 2022. The following table presents the contractual maturities of the Company’s short-term investments as of December 31, 2022: Amortized cost Estimated fair value Due within one year $ 398.6 $ 393.5 Due between one to three years 556.8 531.8 Due after three years 203.1 185.3 Total $ 1,158.5 $ 1,110.6 The Company had 710 short-term investments in unrealized loss positions as of December 31, 2022. There were no material gains or losses from short-term investments that were reclassified out of accumulated other comprehensive loss for the year ended December 31, 2022. As of December 31, 2022, the Company’s short-term investments portfolio consisted of nine security types, seven of which were in an unrealized loss position. The Company’s short-term investments had unrealized losses of approximately $48.2 million as of December 31, 2022. The following tables present the breakdown of the short-term investments that have been in a continuous unrealized loss position aggregated by investment category, as of December 31, 2022 and December 31, 2021: As of December 31, 2022 Less than 12 months More than 12 months Total Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Corporate notes and obligations $ 176.5 $ (3.5) $ 292.3 $ (19.2) $ 468.8 $ (22.7) U.S. Treasury securities 110.9 (1.8) 176.9 (12.2) 287.8 (14.0) Asset backed securities 13.7 (0.4) 90.4 (5.6) 104.1 (6.0) Municipal securities 9.3 (0.3) 51.6 (3.8) 60.9 (4.1) U.S. agency obligations 3.9 — 13.8 (0.8) 17.7 (0.8) Foreign government obligations — — 5.5 (0.4) 5.5 (0.4) Supranational securities — — 3.2 (0.2) 3.2 (0.2) Total $ 314.3 $ (6.0) $ 633.7 $ (42.2) $ 948.0 $ (48.2) As of December 31, 2021 Less than 12 months More than 12 months Total Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Corporate notes and obligations $ 498.6 $ (4.0) $ — $ — $ 498.6 $ (4.0) U.S. Treasury securities 218.0 (2.9) — — 218.0 (2.9) Asset backed securities 120.7 (1.2) — — 120.7 (1.2) Municipal securities 66.0 (0.7) — — 66.0 (0.7) U.S. agency obligations 14.4 (0.2) — — 14.4 (0.2) Foreign government obligations 15.4 (0.1) — — 15.4 (0.1) Supranational securities 7.9 (0.1) — — 7.9 (0.1) Total $ 941.0 $ (9.2) $ — $ — $ 941.0 $ (9.2) Unrealized losses on short-term investments have not been recorded into income because management does not intend to sell nor will be required to sell these securities prior to their anticipated recovery, and for which the decline in fair value is largely due to changes in interest rates. The credit ratings associated with the corporate notes and obligations are mostly unchanged, are highly rated and the issuers continue to make timely principal and interest payments. The Company recorded $15.7 million, $7.5 million, and $12.5 million in interest income from its cash, cash equivalents and short-term investments for the years ended December 31, 2022, 2021 and 2020, respectively.

Fair Value Measurements

Fair Value Measurements	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Fair Value Measurements	Fair Value MeasurementsThe Company measures its financial instruments at fair value each reporting period using a fair value hierarchy that prioritizes the use of observable inputs and minimizes the use of unobservable inputs when measuring fair value. A financial instrument’s classification within the fair value hierarchy is based upon the lowest level of input that is significant to the fair value measurement. The following table presents information about the Company’s financial instruments that are measured at fair value on a recurring basis using the input categories discussed in Note 1: As of December 31, 2022 Level 1 Level 2 Level 3 Total Cash equivalents Money market funds $ 139.5 $ — $ — $ 139.5 Commercial paper — 3.2 — $ 3.2 Total cash equivalents 139.5 3.2 — 142.7 Short-term investments Corporate notes and obligations — 489.5 — 489.5 U.S. Treasury securities — 346.4 — 346.4 Asset backed securities — 111.6 — 111.6 Municipal securities — 61.2 — 61.2 Commercial paper — 46.4 — 46.4 Certificates of deposit — 29.1 — 29.1 Foreign government obligations — 5.6 — 5.6 U.S. agency obligations — 17.6 — 17.6 Supranational securities — 3.2 — 3.2 Total short-term investments — 1,110.6 — 1,110.6 Total $ 139.5 $ 1,113.8 $ — $ 1,253.3 As of December 31, 2021 Level 1 Level 2 Level 3 Total Cash equivalents Money market funds $ 390.3 $ — $ — $ 390.3 Total Cash Equivalents $ 390.3 $ — $ — $ 390.3 Short-term investments Corporate notes and obligations — 603.8 — 603.8 U.S. Treasury securities — 237.5 — 237.5 Asset backed securities — 139.6 — 139.6 Municipal securities — 69.8 — 69.8 U.S. agency obligations — 14.4 — 14.4 Commercial paper — 61.7 — 61.7 Supranational securities — 7.9 — 7.9 Foreign government obligations — 18.3 — 18.3 Certificates of deposit — 32.1 — 32.1 Total short-term investments — 1,185.1 — 1,185.1 Total $ 390.3 $ 1,185.1 $ — $ 1,575.4 As of December 31, 2021, the Company had an investment in a non-marketable equity security in a privately held Company without a readily determinable market value. The investment had a carrying value of $5.6 million and was categorized as Level 3 as of December 31, 2021. The investment was sold during the twelve months ended December 31, 2022 resulting in a gain of $5.0 million. The Company had no transfers between levels of the fair value hierarchy. The carrying amounts of certain financial instruments, including cash held in banks, accounts receivable and accounts payable approximate fair value due to their short-term maturities and are excluded from the fair value table above. The Company had $695.8 million in aggregate principal amount of 0% convertible senior notes due in 2026 (the "2026 Notes"), and $693.3 million in aggregate principal amount of 0% convertible senior notes due in 2028 (the "2028 Notes" and together with the 2026 Notes, the "Notes"), outstanding as of December 31, 2022. Refer to Note 8 "Debt" for further details on the 2026 Notes and 2028 Notes. The estimated fair value of the 2026 Notes and the 2028 Notes, based on a market approach as of December 31, 2022 was approximately $631.5 million and $632.2 million, respectively. The Notes were categorized as Level 2 instruments as the estimated fair value was determined based on the estimated or actual bids and offers of the Notes in an over-the-counter market on the last business day of the period.

Property and Equipment, Net

Property and Equipment, Net	12 Months Ended
	Dec. 31, 2022
Property, Plant and Equipment [Abstract]
Property and Equipment, Net	Property and Equipment, Net Property and equipment, net consisted of the following: As of December 31, 2022 2021 Datacenter and other computer equipment $ 671.3 $ 634.5 Furniture and fixtures 19.8 21.7 Leasehold improvements 118.0 106.7 Construction in progress 2.8 11.7 Total property and equipment 811.9 774.6 Accumulated depreciation and amortization (503.5) (452.6) Property and equipment, net $ 308.4 $ 322.0 The Company leases certain infrastructure, computer equipment, and furniture from various third parties, through equipment finance leases. Infrastructure assets as of December 31, 2022 and 2021, respectively, included a total of $456.4 million and $469.4 million acquired under finance lease agreements. These leases are capitalized in property and equipment, and the related amortization of assets under finance leases is included in depreciation and amortization expense. The accumulated depreciation of the equipment under finance leases totaled $240.9 million and $237.6 million as of December 31, 2022 and 2021, respectively. Depreciation expense related to property and equipment was $140.9 million and $135.7 million for the years ended December 31, 2022 and 2021 respectively.

Business Combinations

Business Combinations	12 Months Ended
	Dec. 31, 2022
Business Combination and Asset Acquisition [Abstract]
Business Combinations	Business Combinations 2022 Business Combination On December 15, 2022, the Company acquired 100% ownership of FormSwift, a cloud-based service that gives individuals and businesses a simple solution to create, complete, edit, and save critical business forms and agreements. The Company believes the combination of Dropbox, Dropbox Sign, DocSend, and FormSwift will help customers across industries manage end-to-end document workflows—from content collaboration to sharing and e-signature—giving them more control over their most important agreements. The results of FormSwift's operations have been included in the Company’s consolidated results of operations since the date of acquisition and were immaterial for the periods presented. The purchase consideration transferred consisted of the following: Purchase consideration Cash paid to stockholders $ 50.0 Cash paid for extinguishing shadow stock units 3.2 Transaction costs paid by Dropbox on behalf of FormSwift 2.0 Cash purchase consideration $ 55.2 Indemnification holdback (1) 14.3 Total purchase consideration $ 69.5 (1) Approximately $14.3 million of the total purchase consideration was withheld as an indemnification holdback to be used for the purpose of satisfying any indemnification claims made by the Company for a period of 18 months following the transaction close date. Any remaining indemnity will be released to the seller's representative following the 18 month period. In addition to the total purchase consideration above, the Company has compensation agreements with key FormSwift personnel consisting of $25.7 million in cash payments subject to ongoing employee service. The related expenses are recognized within research and development expenses over the required service period of three years. The cash payment was transferred to a paying agent escrow account immediately upon the acquisition close date. The related payments will be paid out by the escrow agent as they vest. The purchase consideration was allocated to the tangible and intangible assets and liabilities acquired as of the acquisition date, with the excess recorded to goodwill as shown below. The fair value of assets and liabilities acquired may change as additional information is received during the measurement period. The measurement period will end no later than one-year from the acquisition date. Assets acquired: Cash and cash equivalents $ 0.4 Acquisition-related intangible assets 41.2 Accounts receivable, prepaid and other assets 3.4 Total assets acquired $ 45.0 Liabilities assumed: Accounts payable, accrued and other liabilities $ 4.6 Deferred revenue 6.6 Total liabilities assumed 11.2 Net assets acquired, excluding goodwill 33.8 Total purchase consideration 69.5 Goodwill (2) $ 35.7 (2) The goodwill recognized was primarily attributable to the opportunity to expand the user base of the Company's platform. A portion of the goodwill is deductible for U.S. federal income tax purposes. The fair value of the separately identifiable finite-lived intangible assets acquired and estimated weighted average useful lives are as follows: Estimated fair values Estimated weighted average useful lives Developed technology $ 24.2 5.0 Customer relationships 16.4 2.0 Trade name 0.6 1.0 Total acquisition-related intangible assets $ 41.2 The fair values of the acquisition-related intangible assets were determined using the following methodologies: the multi-period excess earnings method for developed technology, the with and without method for customer relationships, and the relief from royalty method for the trade name, respectively. The valuation model inputs required the application of significant judgment by management. The acquired intangible assets have a total weighted average amortization period of 3.7 years. One-time acquisition-related diligence costs of $1.3 million were expensed within general and administrative expenses as incurred during the year ended December 31, 2022. 2021 Business Combination On March 22, 2021, the Company acquired all outstanding stock of DocSend, a secure document sharing and analytics company. The Company believes the combination of Dropbox, Dropbox Sign, and DocSend will help customers across industries manage end-to-end document workflows—from content collaboration to sharing and e-signature—giving them more control over their business results. The results of DocSend's operations have been included in the Company’s consolidated results of operations since the date of acquisition. The purchase consideration transferred consisted of the following: Purchase consideration Cash paid to common and preferred stockholders and vested option holders $ 125.5 Transaction costs paid by Dropbox on behalf of DocSend 5.0 Fair value of assumed DocSend options attributable to pre-combination services (1) 1.2 Purchase price adjustments 0.1 Total purchase consideration $ 131.8 (1) The fair value of options assumed was based upon the Black-Scholes option-pricing model. In addition to the total purchase consideration above, the Company has compensation agreements with key DocSend personnel consisting of $30.7 million in cash payments subject to ongoing employee service. The related expenses are recognized within sales and marketing and research and development expenses over the required service period of approximately three years. The payments began in the first quarter of 2022, with $10.2 million paid during the year ended December 31, 2022. The remaining balance of $20.5 million will be paid out over the next year in accordance with the acquisition agreement. The purchase consideration was allocated to the tangible and intangible assets and liabilities acquired as of the acquisition date, with the excess recorded to goodwill as shown below. Assets acquired: Cash and cash equivalents $ 5.1 Acquisition-related intangible assets 20.6 Accounts receivable, prepaid and other assets 6.1 Total assets acquired $ 31.8 Liabilities assumed: Accounts payable, accrued and other liabilities $ 6.4 Deferred revenue 1.9 Deferred tax liability 1.9 Total liabilities assumed 10.2 Net assets acquired, excluding goodwill 21.6 Total purchase consideration 131.8 Goodwill (2) $ 110.2 (2) The goodwill recognized was primarily attributable to the opportunity to expand the user base of the Company's platform. The goodwill is not deductible for U.S. federal income tax purposes. The fair value of the separately identifiable finite-lived intangible assets acquired and estimated weighted average useful lives are as follows: Estimated fair values Estimated weighted average useful lives Developed technology $ 11.5 5.0 Customer relationships 8.1 5.0 Trade name 1.0 5.0 Total acquisition-related intangible assets $ 20.6 The fair values of the acquisition-related intangible assets were determined using the following methodologies: the multi-period excess earnings method for customer relationships, and the relief from royalty method for developed technology, and the trade name, respectively. The valuation model inputs required the application of significant judgment by management. The acquired intangible assets have a total weighted average amortization period of 5.0 years. One-time acquisition-related diligence costs of $1.2 million were expensed within general and administrative expenses as incurred during the year ended December 31, 2021.

Intangible Assets

Intangible Assets	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Intangible Assets	Intangible Assets Intangible assets consisted of the following: As of December 31, Weighted- (In years) 2022 2021 Developed technology $ 74.3 $ 45.9 4.2 Customer relationships 43.2 28.6 2.2 Patents 19.4 19.5 4.3 Software 8.9 9.0 0.7 Trademarks and trade names 5.8 5.6 1.6 Licenses 4.6 4.6 0.0 Assembled workforce in asset acquisitions 3.4 3.0 3.3 Other 1.1 0.8 2.8 Total intangibles 160.7 117.0 Accumulated amortization (72.4) (63.4) Intangible assets, net $ 88.3 $ 53.6 Amortization expense was $16.3 million, $15.6 million, and $14.1 million for the years ended December 31, 2022, 2021, and 2020, respectively. Expected future amortization expense for intangible assets as of December 31, 2022, is as follows: 2023 $ 30.4 2024 25.1 2025 14.8 2026 10.4 2027 7.0 Thereafter 0.6 Total $ 88.3

Goodwill

Goodwill	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Goodwill	Goodwill Goodwill represents the excess of the purchase price in a business combination over the fair value of net tangible and intangible assets acquired. The changes in the carrying amounts of goodwill were as follows: Balance at December 31, 2021 $ 356.6 FormSwift acquisition 35.7 Other acquisition 14.4 Effect of foreign currency translation (3.4) Balance at December 31, 2022 $ 403.3

Debt

Debt	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Debt	Debt Revolving credit facility In February 2018, the Company entered into an amendment to the revolving credit facility to, among other things, permit the Company to make certain investments, enter into an unsecured standby letter of credit facility and increase its standby letter of credit sublimit to $187.5 million. The Company increased its borrowing capacity under the revolving credit facility from $600.0 million to $725.0 million. In February 2021, the Company amended the revolving credit facility to decrease its borrowing capacity under the revolving credit facility from $725.0 million to $500.0 million and extended the term of the agreement through February 2026. The Company may from time to time request increases in its borrowing capacity under the revolving credit facility of up to $250.0 million, provided no event of default has occurred or is continuing or would result from such increase. In conjunction with the February 2021 amendment, the Company paid upfront issuance fees of $1.7 million, which are being amortized over the remaining term of the agreement , and wrote-off $0.2 million in unamortized deferred debt issuance costs. Pursuant to the terms of the revolving credit facility, the Company may issue letters of credit under the revolving credit facility, which reduce the total amount available for borrowing. Pursuant to the terms of the revolving credit facility, the Company is required to pay an annual commitment fee that accrues at a rate of 0.20% per annum on the unused portion of the borrowing commitments under the revolving credit facility. In addition, the Company is required to pay a fee in connection with letters of credit issued under the revolving credit facility, which accrues at a rate of 1.375% per annum on the amount of such letters of credit outstanding. There is an additional fronting fee of 0.125% per annum multiplied by the average aggregate daily maximum amount available under all letters of credit. Borrowings under the revolving credit facility bear interest, at the Company’s option, at an annual rate based on LIBOR plus a spread of 1.375% or at an alternative base rate plus a spread of 0.375%. The revolving credit facility contains customary conditions to borrowing, events of default and covenants, including covenants that restrict the Company’s ability to incur indebtedness, grant liens, make distributions to holders of the Company or its subsidiaries’ equity interests, make investments, or engage in transactions with its affiliates. In addition, the revolving credit facility contains financial covenants, including a consolidated leverage ratio incurrence covenant and a minimum liquidity balance of $100.0 million, which includes any available borrowing capacity. The Company was in compliance with the covenants of the revolving credit facility as of December 31, 2022 and 2021, respectively. The Company had an aggregate of $40.6 million of letters of credit outstanding under the revolving credit facility as of December 31, 2022, and the Company’s total available borrowing capacity under the revolving credit facility was $459.4 million as of December 31, 2022. The Company’s letters of credit have final expiration dates through 2036. Convertible senior notes During the first quarter of 2021, the Company issued $695.8 million aggregate principal amount of the 2026 Notes. Additionally, during the first quarter of 2021, the Company issued $693.3 million aggregate principal amount of the 2028 Notes. The Notes were issued in a private placement to qualified institutional buyers pursuant to Rule 144A under the Securities Act of 1933. The net proceeds from the sale of the Notes were approximately $1.4 billion after deducting offering and issuance costs related to the Notes. The Notes of each series do not bear regular interest. The Notes of each series may bear special interest as the remedy relating to the Company’s failure to comply with certain of its reporting obligations. The Company has complied with these reporting obligations from the issuance date through December 31, 2022. The 2026 Notes will mature on March 1, 2026, and the 2028 Notes will mature on March 1, 2028, in each case, unless earlier converted, redeemed or repurchased. The initial conversion rate for the 2026 Notes is 26.1458 shares of the Company’s Class A common stock per $1,000 principal amount of such Note, which is equivalent to an initial conversion price of approximately $38.25 per share. The initial conversion rate for the 2028 Notes is 28.2889 shares of Class A common stock per $1,000 principal amount of such Notes, which is equivalent to an initial conversion price of approximately $35.35 per share. The conversion rate for each series of Notes will be subject to adjustment upon the occurrence of certain specified events but will not be adjusted for accrued and unpaid special interest. In addition, upon the occurrence of a make-whole fundamental change (as defined in the relevant indentures governing the Notes) or a notice of redemption, the Company will, in certain circumstances, increase the conversion rate of the relevant series of Notes by a number of additional shares for a holder that elects to convert all or a portion of its Notes of such series in connection with such make-whole fundamental change or who elects to convert such Notes that are subject to such notice of redemption. The conversion rate for the 2026 Notes and the 2028 Notes shall not exceed 43.1406 shares per $1,000 principal amount of such Notes, subject to certain customary anti-dilution adjustments (as defined in the relevant indentures governing the Notes). There have been no changes to the initial conversion price of the Notes since issuance as of December 31, 2022. Upon conversion, the principal portion of the Notes of the applicable series being converted will be settled in cash, and any amount in excess of the principal portion of such Notes will be settled in cash or shares of the Company’s Class A common stock or any combination thereof at the Company’s option. The if-converted value of the 2026 Notes and the 2028 Notes was below the principal value of the respective Notes as of December 31, 2022. In addition, during the year ended December 31, 2022, the conditions allowing holders of the Notes to convert were not met. As a result, the Notes are not convertible during the year ended December 31, 2022. Prior to the close of business on the business day immediately preceding December 1, 2025, in the case of the 2026 Notes, and prior to the close of business on the business day immediately preceding December 1, 2027, in the case of the 2028 Notes, the Notes of the applicable series will be convertible only under the following circumstances: (1) during any calendar quarter commencing after June 30, 2021 (and only during such calendar quarter), if the last reported sale price of the Class A common stock for at least 20 trading days (whether or not consecutive) during the 30 consecutive trading day period ending on the last trading day of the immediately preceding calendar quarter is greater than or equal to 130% of the conversion price for the relevant series of Notes on each applicable trading day; (2) during the five business day period after any five consecutive trading day period in which, for each trading day of that period, the trading price per $1,000 principal amount of 2026 Notes or 2028 Notes, as applicable, for such trading day was less than 98% of the product of the last reported sale price of the Class A common stock and the conversion rate for such series of Notes on each such trading day; (3) if the Company calls any or all of the Notes for redemption, such Notes of the applicable series called for redemption may be converted at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date; or (4) upon the occurrence of specified corporate transactions. On or after December 1, 2025, in the case of the 2026 Notes, and on or after December 1, 2027, in the case of the 2028 Notes, until the close of business on the second scheduled trading day immediately preceding the relevant maturity date, holders of the relevant series of Notes may convert all or a portion of their Notes of such series regardless of the foregoing conditions. The Company may redeem for cash all or any part of the Notes, at its option, on or after March 6, 2024, in the case of the 2026 Notes, and on or after March 6, 2025, in the case of the 2028 Notes, if the last reported sale price of its Class A common stock has been at least 130% of the conversion price for the relevant series of Notes then in effect for at least 20 trading days (whether or not consecutive) during any 30 consecutive trading day period (including the last trading day of such period) ending on, and including, the trading day immediately preceding the date on which the Company provides notice of redemption at a redemption price equal to 100% of the principal amount of the series of Notes to be redeemed, plus any accrued and unpaid special interest to, but excluding, the redemption date. No sinking fund is provided for the Notes. Upon the occurrence of a fundamental change (as defined in the relevant indentures governing the Notes) prior to the relevant maturity date, holders of the relevant series of Notes may require the Company to repurchase all or a portion of the Notes of such series for cash at a price equal to 100% of the principal amount of the series of Notes to be repurchased, plus any accrued and unpaid special interest to, but excluding, the fundamental change repurchase date. Additionally, and upon events of default (as defined in the relevant indentures governing the Notes), the maturity of the Notes may be accelerated. The Notes are the Company’s general unsecured obligations and will rank senior in right of payment to any existing and future indebtedness that is contractually subordinated to the Notes; rank equal in right of payment with the Company’s existing and future senior unsecured indebtedness that is not so subordinated; effectively rank junior in right of payment to any of the Company’s existing and future secured indebtedness to the extent of the value of the assets securing such indebtedness; and be structurally subordinated to all indebtedness and other liabilities (including trade payables) of subsidiaries of the Company. In accounting for the Notes, issuance costs of $11.0 million and $11.0 million for the 2026 Notes and the 2028 Notes were deducted from the carrying value of the Notes in the consolidated balance sheet. Issuance costs will be recognized as interest expense over the five-year term and seven-year term for the 2026 Notes and the 2028 Notes, respectively. The following is a summary of the Company’s convertible senior notes as of December 31, 2022 and December 31, 2021. 2026 Notes 2028 Notes Total December 31, 2022 Principal balance $ 695.8 $ 693.3 $ 1,389.1 Unamortized issuance costs (7.0) (8.1) (15.1) Carrying value, net $ 688.8 $ 685.2 $ 1,374.0 December 31, 2021 Principal balance $ 695.8 $ 693.3 $ 1,389.1 Unamortized issuance costs (9.1) (9.7) (18.8) Carrying value, net $ 686.7 $ 683.6 $ 1,370.3 During the years ended December 31, 2022 and 2021, the Company recognized $2.1 million and $1.9 million in interest expense for the 2026 Notes and $1.6 million and $1.3 million in interest expense for the 2028 Notes, respectively, with such interest expense solely consisting of amortization of issuance costs. The effective interest rate for the 2026 Notes and the 2028 Notes was 0.32% and 0.22%, respectively, as of December 31, 2022. Maturities on the Company's long-term convertible debt are as follows: Convertible Debt 2023 $ — 2024 — 2025 — 2026 695.8 2027 — Thereafter 693.3 Total 1,389.1 Convertible Note Hedges and Warrants Concurrent with the offering of the Notes, the Company entered into convertible note hedge transactions with certain counterparties whereby the Company had the option to purchase a total of approximately 18.2 million shares for note hedges expiring in March 2026 (the “2026 Note Hedges”) and 19.6 million shares for note hedges expiring in March 2028 (the “2028 Note Hedges”, together with the 2026 Note Hedges, the “Note Hedges”), respectively, of its common stock at a price of approximately $38.25 and $35.35 per share, respectively. The aggregate cost of the convertible note hedge transactions was $265.3 million. The Note Hedges, or a portion thereof, are exercisable upon conversion of the Notes and the satisfaction of certain conditions set forth in the Note Hedges. Additionally, the Note Hedges may be terminated and early settled upon the occurrence of certain events, including certain merger events, events of default, and upon a fundamental change (as defined in the relevant indentures for the Notes). The Note Hedges are settleable in cash, shares or a combination of cash and shares, at the option of the Company, and the settlement alternative will be the same as the settlement alternative of the conversion spread for the respective Notes. The convertible note hedge transactions are expected generally to reduce the potential dilution to the Class A common stock upon conversion of the relevant series of Notes and/or offset any cash payments the Company is required to make in excess of the principal amount of such converted Notes, as the case may be, in the event that the market price per share of the Class A common stock, as measured under the terms of the convertible note hedge transactions, is greater than the applicable strike price of those convertible note hedge transactions. As of December 31, 2022, the Company’s stock price was below the exercise price of the respective Note Hedges. In addition, the Company sold warrants to certain counterparties whereby the holders of the warrants had the option to purchase a total of approximately 18.1 million shares underlying warrants expiring in 2026 (the “2026 Warrants”) and 20.1 million shares underlying warrants expiring in 2028 (the “2028 Warrants”, together with the 2026 Warrants, the “Warrants”), respectively, of the Company’s Class A common stock at an initial strike price of $46.36 and $46.36 per share, respectively. The Company received aggregate cash proceeds of $202.9 million from the sale of these Warrants. If the market price per share of the Company’s Class A common stock, as measured under the terms of the Warrants, exceeds the strike price of the Warrants, the Warrants could have a dilutive effect, unless the Company elects, subject to certain conditions, to settle the Warrants in cash. The Warrants are only exercisable on the applicable expiration dates in accordance with the terms of the Warrants. Subject to the other terms of the Warrants, the first expiration date applicable to the 2026 Warrants and to the 2028 Warrants is June 1, 2026, and June 1, 2028, respectively, and the final expiration date applicable to the 2026 Warrants and 2028 Warrants is August 10, 2026 and August 10, 2028, respectively. As of December 31, 2022, the Company’s Class A common stock price was below the exercise price of the Warrants. Taken together, the purchase of the Note Hedges and the sale of the Warrants are intended to reduce potential dilution from the conversion of the 2026 Notes and the 2028 Notes, and to effectively increase the overall conversion price from $38.25 per share to $46.36 per share and from $35.35 per share to $46.36 for the 2026 Notes and the 2028 Notes, respectively. The Note Hedges and the Warrants are equity-classified instruments as a result of being indexed to the Company’s Class A common stock and meeting certain equity classification criteria, and the instruments will not be remeasured in subsequent periods as long as the instruments continue to meet these accounting criteria. The premium paid for the Note Hedges has been included as a net reduction to additional paid-in capital within stockholders’ (deficit) equity, and the premium received for the Warrants has been included as a net increase to additional paid-in capital within stockholders' (deficit) equity.

Leases

Leases	12 Months Ended
	Dec. 31, 2022
Leases [Abstract]
Leases	Leases Leases The Company has operating leases for corporate offices and datacenters, and finance leases for infrastructure and office equipment. The Company’s leases have remaining lease terms of 1 year to 14 years, some of which include options to extend the leases for up to 5 years. The Company also has subleases for several floors of its former corporate offices. The Company classifies its subleases as operating leases. The subleases have remaining lease terms of 1 year to 10 years, some of which include options to extend the sublease for up to approximately 4 years. Sublease income, which is recorded as a reduction of rental expense, was $20.1 million for the year ended December 31, 2022 and $17.6 million for the year ended December 31, 2021. The components of lease cost were as follows: Year ended December 31, 2022 2021 Operating lease cost (1) $ 91.7 $ 107.8 Finance lease cost: Amortization of assets under finance lease 111.4 107.1 Interest 7.5 8.8 Total finance lease cost $ 118.9 $ 115.9 (1) Is presented gross of sublease income and includes short-term leases, which are immaterial. Other information related to leases was as follows: Year ended December 31, 2022 Year ended December 31, 2021 Supplemental Cash Flow Information: Cash paid for amounts included in the measurement of lease liabilities: Payments for operating leases included in cash from operating activities $ 104.7 $ 130.3 Payments for finance leases included in cash from operating activities 7.5 8.8 Payments for finance leases included in cash from financing activities 127.5 110.4 Assets obtained in exchange for lease obligations: Operating leases 33.0 67.1 Finance leases $ 105.8 $ 127.3 As of December 31, 2022 As of December 31, 2021 Weighted Average Remaining Lease Term (in years) Operating leases 9.9 10.2 Finance leases 2.6 2.7 Weighted Average Discount Rate Operating leases 4.1 % 4.0 % Finance leases 3.4 % 2.9 % Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future non-cancelable rent payments from the Company's subtenants as of December 31, 2022 were as follows: Year ending December 31, Operating leases 2023 17.5 2024 16.7 2025 15.6 2026 11.9 2027 8.2 Thereafter 26.4 Total future sublease rent payments 96.3 Less subtenant incentive (1.1) Total future sublease rent payments, net $ 95.2 In 2017, the Company signed a 15 year lease agreement for office space in San Francisco, California, to serve as its corporate headquarters which commenced in 2018. The Company’s obligations under the lease are supported by a $26.1 million letter of credit, which reduced the borrowing capacity under the revolving credit facility. As of December 31, 2022, the Company's remaining minimum obligation for its headquarters was $553.2 million. In the fourth quarter of 2020, the Company announced a Virtual First work model pursuant to which remote work has become the primary experience for all of its employees. As part of the Virtual First strategy, Dropbox retained a portion of its office space to be used for the Company’s team collaboration use and a portion will be marketed for sublease. The Company evaluated certain of its right-of-use assets and other lease related assets including leasehold improvements, furniture and fixtures, and computer equipment for impairment under ASC 360. During the years ended December 31, 2022 and 2021, the Company continued to evaluate the recoverability of its real estate assets and made adjustments to market participant assumptions. In the fourth quarter of 2022, the Company determined that there were adverse changes in the corporate real estate markets where it plans to sublease office space. These changes have reduced demand for corporate office real estate, which the Company expects will result in increased real estate vacancy periods and reduced sublease rent rates. Accordingly, the Company assessed the recoverability of its real estate assets in the markets that have been impacted. As a result of this analysis, the Company reassessed its real estate asset groups and estimated the fair value of the office space to be subleased using current market conditions. Where the carrying value of the individual asset groups exceeded their fair value, an impairment charge was recognized for the difference. The Company recorded impairment charges related to real estate assets of $175.2 million and $31.3 million during the year ended December 31, 2022 and 2021, respectively. The impairment charges included accruals for expected losses related to common area maintenance costs that the Company expects to incur during vacancy periods. Accruals for expected losses are recorded within accrued and other current liabilities and other liabilities. As of December 31, 2022, the Company has a $1.0 million commitment related to a sublease that has not commenced, with a lease term of 2 years.
Leases	Leases Leases The Company has operating leases for corporate offices and datacenters, and finance leases for infrastructure and office equipment. The Company’s leases have remaining lease terms of 1 year to 14 years, some of which include options to extend the leases for up to 5 years. The Company also has subleases for several floors of its former corporate offices. The Company classifies its subleases as operating leases. The subleases have remaining lease terms of 1 year to 10 years, some of which include options to extend the sublease for up to approximately 4 years. Sublease income, which is recorded as a reduction of rental expense, was $20.1 million for the year ended December 31, 2022 and $17.6 million for the year ended December 31, 2021. The components of lease cost were as follows: Year ended December 31, 2022 2021 Operating lease cost (1) $ 91.7 $ 107.8 Finance lease cost: Amortization of assets under finance lease 111.4 107.1 Interest 7.5 8.8 Total finance lease cost $ 118.9 $ 115.9 (1) Is presented gross of sublease income and includes short-term leases, which are immaterial. Other information related to leases was as follows: Year ended December 31, 2022 Year ended December 31, 2021 Supplemental Cash Flow Information: Cash paid for amounts included in the measurement of lease liabilities: Payments for operating leases included in cash from operating activities $ 104.7 $ 130.3 Payments for finance leases included in cash from operating activities 7.5 8.8 Payments for finance leases included in cash from financing activities 127.5 110.4 Assets obtained in exchange for lease obligations: Operating leases 33.0 67.1 Finance leases $ 105.8 $ 127.3 As of December 31, 2022 As of December 31, 2021 Weighted Average Remaining Lease Term (in years) Operating leases 9.9 10.2 Finance leases 2.6 2.7 Weighted Average Discount Rate Operating leases 4.1 % 4.0 % Finance leases 3.4 % 2.9 % Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future non-cancelable rent payments from the Company's subtenants as of December 31, 2022 were as follows: Year ending December 31, Operating leases 2023 17.5 2024 16.7 2025 15.6 2026 11.9 2027 8.2 Thereafter 26.4 Total future sublease rent payments 96.3 Less subtenant incentive (1.1) Total future sublease rent payments, net $ 95.2 In 2017, the Company signed a 15 year lease agreement for office space in San Francisco, California, to serve as its corporate headquarters which commenced in 2018. The Company’s obligations under the lease are supported by a $26.1 million letter of credit, which reduced the borrowing capacity under the revolving credit facility. As of December 31, 2022, the Company's remaining minimum obligation for its headquarters was $553.2 million. In the fourth quarter of 2020, the Company announced a Virtual First work model pursuant to which remote work has become the primary experience for all of its employees. As part of the Virtual First strategy, Dropbox retained a portion of its office space to be used for the Company’s team collaboration use and a portion will be marketed for sublease. The Company evaluated certain of its right-of-use assets and other lease related assets including leasehold improvements, furniture and fixtures, and computer equipment for impairment under ASC 360. During the years ended December 31, 2022 and 2021, the Company continued to evaluate the recoverability of its real estate assets and made adjustments to market participant assumptions. In the fourth quarter of 2022, the Company determined that there were adverse changes in the corporate real estate markets where it plans to sublease office space. These changes have reduced demand for corporate office real estate, which the Company expects will result in increased real estate vacancy periods and reduced sublease rent rates. Accordingly, the Company assessed the recoverability of its real estate assets in the markets that have been impacted. As a result of this analysis, the Company reassessed its real estate asset groups and estimated the fair value of the office space to be subleased using current market conditions. Where the carrying value of the individual asset groups exceeded their fair value, an impairment charge was recognized for the difference. The Company recorded impairment charges related to real estate assets of $175.2 million and $31.3 million during the year ended December 31, 2022 and 2021, respectively. The impairment charges included accruals for expected losses related to common area maintenance costs that the Company expects to incur during vacancy periods. Accruals for expected losses are recorded within accrued and other current liabilities and other liabilities. As of December 31, 2022, the Company has a $1.0 million commitment related to a sublease that has not commenced, with a lease term of 2 years.

Commitments and Contingencies

Commitments and Contingencies	12 Months Ended
	Dec. 31, 2022
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	Commitments and Contingencies Other commitments Other commitments include payments to third-party vendors for services related to the Company's infrastructure, infrastructure warranty contracts, and asset retirement obligations for office modifications. Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details. Legal matters From time to time, the Company is a party to a variety of claims, lawsuits, and proceedings which arise in the ordinary course of business, including claims of alleged infringement of intellectual property rights. The Company records a liability when it believes that it is probable that a loss will be incurred and the amount of loss or range of loss can be reasonably estimated. In its opinion, resolution of pending matters is not likely to have a material adverse impact on its consolidated results of operations, cash flows, or its financial position. Given the unpredictable nature of legal proceedings, the Company bases its estimate on the information available at the time of the assessment. As additional information becomes available, the Company reassesses the potential liability and may revise the estimate. In 2019, multiple lawsuits were filed against the Company in California state court and federal court asserting violations of federal securities laws, for allegedly making materially false and misleading statements in, or omitting material information from, the Company's initial public offering ("IPO") registration statement. All cases have now been resolved. The federal court litigation was resolved in a settlement approved in December 2021. In the state court, the Company’s motion to dismiss the consolidated case based on the exclusive federal forum provisions contained in the Company's amended and restated bylaws was granted on December 4, 2020, and affirmed by the California Court of Appeal on May 13, 2022. The California Supreme Court denied the plaintiff’s petition for review on August 10, 2022. The plaintiff elected not to petition for certiorari to the U.S. Supreme Court. Accordingly, the state securities litigation is also now resolved. Indemnification The Company’s arrangements generally include certain provisions for indemnifying customers against liabilities if its products or services infringe a third party’s intellectual property rights. It is not possible to determine the maximum potential amount under these indemnification obligations due to the limited history of prior indemnification claims.

Accrued and Other Current Liabi

Accrued and Other Current Liabilities	12 Months Ended
	Dec. 31, 2022
Payables and Accruals [Abstract]
Accrued and Other Current Liabilities	Accrued and Other Current Liabilities Accrued and other current liabilities consisted of the following: As of December 31, 2022 2021 Non-income taxes payable $ 76.4 $ 77.4 Accrued legal and other external fees 25.5 24.0 Other accrued and current liabilities 38.0 39.4 Total accrued and other current liabilities $ 139.9 $ 140.8

Stockholders_ (Deficit) Equity

Stockholders’ (Deficit) Equity	12 Months Ended
	Dec. 31, 2022
Stockholders' Equity Note [Abstract]
Stockholders’ (Deficit) Equity	Stockholders’ (Deficit) Equity Common stock The Company’s amended and restated certificate of incorporation authorizes the issuance of Class A common stock, Class B common stock, and Class C common stock. Holders of Class A common stock, Class B common stock, and Class C common stock are entitled to dividends on a pro rata basis, when, as, and if declared by the Company’s Board of Directors, subject to the rights of the holders of the Company’s preferred stock. Holders of Class A common stock are entitled to one vote per share, holders of Class B common stock are entitled to 10 votes per share, and holders of Class C common stock are entitled to zero votes per share. As of December 31, 2022, the Company had authorized 2,400.0 million shares of Class A common stock, 475.0 million shares of Class B common stock, and 800.0 million shares of Class C common stock, each at par value of $0.00001. Holders of Class B common stock voluntarily converted 0.6 million and 0.7 million shares into an equivalent number of shares of Class A common stock during the years ended December 31, 2022 and 2021 respectively. As of December 31, 2022, 267.2 million shares of Class A common stock, 82.2 million shares of Class B common stock, and no shares of Class C common stock were issued and outstanding. As of December 31, 2021, 292.7 million shares of Class A common stock, 82.8 million shares of Class B common stock, and no shares of Class C common stock were issued and outstanding. Class A shares issued and outstanding as of December 31, 2022 and 2021 exclude unvested restricted stock awards granted to certain executives. Class A shares issued and outstanding as of December 31, 2022 and 2021 exclude 8.3 million unvested restricted stock awards granted to one of the Company's co-founders. See "Co-Founder Grant" section below for further details. Preferred stock The Company's Board of Directors will have the authority, without further action by the Company's stockholders, to issue up to 240.0 million shares of undesignated preferred stock with rights and preferences, including voting rights, designated from time to time by the Board of Directors. Stock repurchase program In February 2022, the Board of Directors authorized the Company to repurchase up to $1.2 billion of the Company's outstanding shares of Class A common stock. Share repurchases will be made from time to time in private transactions or open market purchases, as permitted by securities laws and other legal requirements and will be subject to a review of the circumstances in place at that time, including prevailing market prices. The program does not obligate the Company to repurchase any specific number of shares and may be discontinued at any time. During the year ended December 31, 2022, the Company repurchased and subsequently retired 35.6 million shares of its Class A common stock for an aggregate amount of $795.4 million. During the year ended December 31, 2021, the Company repurchased and subsequently retired 41.1 million of its Class A common stock for an aggregate amount of $1.1 billion. This includes $200.0 million in repurchases of 8.6 million shares of our Class A common stock in conjunction with the issuance of the Notes, which was outside of our stock repurchase program. Equity incentive plans Under the 2018 Plan, the Company may grant stock-based awards to purchase or directly issue shares of common stock to employees, directors, and consultants. Options are granted at a price per share equal to the fair market value of the Company's common stock at the date of grant. Options granted are exercisable over a maximum term of 10 years from the date of grant and generally vest over a period of four years. RSUs and RSAs are also granted under the 2018 Plan. The 2018 Plan will terminate 10 years after the later of (i) its adoption or (ii) the most recent stockholder-approved increase in the number of shares reserved under the 2018 Plan, unless terminated earlier by the Company's Board of Directors. The 2018 Plan was adopted on March 22, 2018. In connection with the acquisition of DocSend, the Company assumed unvested stock options and an immaterial number of unvested RSUs that had been granted under DocSend's 2013 Stock Plan and DocSend's 2015 Stock Option and Grant Plan. As of December 31, 2022, there were 34.8 million stock-based awards issued and outstanding and 98.2 million shares available for issuance under the Dropbox Equity Incentive Plans, Dropbox Sign's 2011 Equity Incentive Plan, DocSend's 2013 Stock Plan and DocSend's 2015 Stock Option and Grant Plan (collectively, the "Plans"). Stock option and restricted stock activity for the Plans was as follows for the years ended December 31, 2022 and 2021: Options outstanding Restricted stock Number of Number of Weighted- Weighted- Aggregate Intrinsic Value Number of Weighted- Balance as of December 31, 2020 78.5 1.3 $ 13.73 5.7 $ 11.4 31.9 $ 19.79 Additional shares authorized 20.3 Stock options assumed (1) 0.4 0.4 $ 2.17 Options exercised and restricted stock units and awards released (0.7) 9.77 (12.7) 20.77 Options and restricted stock units and awards canceled 11.0 (0.1) 11.84 (11.0) 21.12 Shares withheld related to net share settlement of restricted stock units and awards 4.6 20.71 Options and restricted stock units and awards granted (19.6) 19.6 26.34 Balance as of December 31, 2021 95.2 0.9 $ 12.09 5.4 $ 10.0 27.8 $ 24.17 Additional shares authorized 18.8 Options exercised and restricted stock units and awards released (0.1) 3.00 (14.3) 23.37 Options and restricted stock units and awards canceled 6.9 (0.4) 18.53 (6.5) 23.72 Shares withheld related to net share settlement of restricted stock units and awards 5.1 23.40 Options and restricted stock units and awards granted (27.8) 27.8 22.68 Balance as of December 31, 2022 98.2 0.4 $ 11.30 4.5 $ 4.5 34.8 $ 23.40 Vested at December 31, 2022 0.3 $ 13.83 4.1 $ 2.8 — $ — Unvested at December 31, 2022 0.1 $ 2.01 $ 1.7 34.8 $ 23.40 (1) This amount includes an immaterial amount of unvested RSUs that were assumed as part of the acquisition of DocSend. The RSUs had a weighted-average grant date fair value of $26.86 per share and a total fair value of $0.4 million, all of which will be recognized as post-combination stock-based compensation expense. The following table summarizes information about the pre-tax intrinsic value of options exercised during the years ended December 31, 2022 and 2021: Year ended 2022 2021 Intrinsic value of options exercised $ 2.9 $ 12.3 As of December 31, 2022, unamortized stock-based compensation related to unvested stock options, restricted stock awards (excluding the Co-Founder Grant), and RSUs was $772.2 million. The weighted-average period over which such compensation expense will be recognized if the requisite service is provided is approximately 2.8 years as of December 31, 2022. Assumed stock options In connection with the acquisition of DocSend the Company assumed 0.9 million unvested stock options which were valued using the Black-Scholes option-pricing model. The fair value of stock options assumed were estimated using the following assumptions: Expected volatility 47 % Expected term (in years) 2.0 - 6.8 Risk-free interest rate 0.15% - 1.29% Dividend yield — % Expected volatility. The expected volatility is based on the Company's historical volatility. Management believes this is the best estimate of the expected volatility over the expected life of its stock options. Expected term. The Company determines the expected term based on the average period the stock options are expected to remain outstanding, generally calculated as the midpoint of the stock options’ remaining vesting term and contractual expiration period, as the Company does not have sufficient historical information to develop reasonable expectations about future exercise patterns and post-vesting employment termination behavior. Risk-free interest rate . The risk-free interest rate is based on the U.S. Treasury security in effect at the time the options were assumed for maturities corresponding with the expected term of the option. Expected dividend yield . The Company has not paid and does not expect to pay dividends. Consequently, the Company uses an expected dividend yield of zero. In connection with the acquisition of DocSend, the estimated weighted-average grant date fair value for stock options assumed was $25.28 per share and a total fair value of $9.3 million, of which, $8.1 million will be recognized as post-combination stock-based compensation expense. Co-Founder Grant In December 2017, the Board of Directors approved the Company's Co-Founder Grant, consisting of 10.3 million shares of Class A common stock in the form of RSAs which were granted to Drew Houston, the Company’s co-founder and Chief Executive Officer. This Co-Founder Grant has service-based, market-based, and performance-based vesting conditions. The Co-Founder Grant is excluded from Class A common stock issued and outstanding until the satisfaction of these vesting conditions. The Co-Founder Grant also provides the holder with certain stockholder rights, such as the right to vote the shares with the other holders of Class A common stock and a right to cumulative declared dividends. The Co-Founder Grant is eligible to vest over the ten-year period following the date the Company’s shares of Class A common stock commenced trading on the Nasdaq Global Select Market in connection with the Company’s IPO. The Co-Founder Grant is comprised of nine tranches that are eligible to vest based on the achievement of stock price goals, each of which are referred to as a Stock Price Target, measured over a consecutive thirty-day trading period during the Performance Period. The Performance Period began on January 1, 2019. During the first four years of the Performance Period, no more than 20% of the shares subject to the Co-Founder Grant would be eligible to vest in any calendar year. After the first four years, all shares are eligible to vest based on the achievement of the Stock Price Targets.

Net Income (Loss) Per Share

Net Income (Loss) Per Share	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Net Income (Loss) Per Share	Net Income (Loss) Per Share The Company computes net income (loss) per share using the two-class method required for multiple classes of common stock and participating securities. The rights, including the liquidation and dividend rights, of the Class A common stock and Class B common stock are substantially identical, other than voting rights. Accordingly, the Class A common stock and Class B common stock share equally in the Company’s net income and losses. Basic net income per share is computed by dividing net income attributable to common stockholders by the weighted-average number of shares of the Class A and Class B common stock outstanding. Diluted net income per share is computed by dividing net income attributable to common stockholders by the weighted-average number of diluted common shares outstanding. The computation of the diluted net income per share of Class A common stock assumes the conversion of our Class B common stock to Class A common stock, while the diluted net income per share of Class B common stock does not assume the conversion of those shares to Class A common stock. The dilutive effect of potentially dilutive common shares is reflected in diluted earnings per share by application of the if-converted method for the 2026 Notes and the 2028 Notes, and by application of the treasury stock method for the Company's other potentially dilutive securities. The numerators and denominators of the basic and diluted EPS computations for our common stock are calculated as follows (in millions, except for per share amounts): Year ended December 31, 2022 2021 Class A Class B Class A Class B Basic net income per share: Numerator Net income attributable to common stockholders $ 426.8 $ 126.4 $ 263.9 $ 71.9 Denominator Weighted-average number of common shares outstanding used in computing basic net income per share 278.6 82.6 304.9 83.1 Net income per common share, basic $ 1.53 $ 1.53 $ 0.87 $ 0.87 Diluted net income per share: Numerator Net income attributable to common stockholders $ 426.8 $ 126.4 $ 263.9 $ 71.9 Reallocation of net income as a result of conversion of Class B to Class A common stock $ 126.4 $ — $ 71.9 $ — Reallocation of net income to Class B common stock $ — $ (0.7) $ — $ (1.3) Net income attributable to common stockholders for diluted EPS $ 553.2 $ 125.7 $ 335.8 $ 70.6 Denominator Weighted-average number of common shares outstanding used in computing basic net income per share 278.6 82.6 304.9 83.1 Weighted-average effect of dilutive restricted stock units and awards and employee stock options 2.1 — 7.8 0.1 Conversion of Class B to Class A common stock 82.6 — 83.1 — Weighted-average number of common shares outstanding used in computing diluted net income per share 363.3 82.6 395.8 83.2 Net income per common share, diluted $ 1.52 $ 1.52 $ 0.85 $ 0.85 The following table sets forth the calculation of basic and diluted net loss per share attributable to common stockholders during the periods presented. The voluntary conversions of Class B common stock into Class A common stock are included in the table below weighted for the respective periods outstanding. Year ended December 31, 2020 Class A Class B Numerator: Net loss attributable to common stockholders $ (182.5) $ (73.8) Denominator: Weighted-average number of common shares outstanding used in computing basic and diluted net loss per common share 295.0 119.3 Net loss per common share, basic and diluted $ (0.62) $ (0.62) Since the Company was in a loss position for the year ended December 31, 2020, basic net loss per share attributable to common stockholders is the same as diluted net loss per share as the inclusion of all potential common shares outstanding would have been anti-dilutive. The weighted-average impact of potentially dilutive securities that were not included in the diluted per share calculations because they would be anti-dilutive was as follows: Year ended December 31, 2022 2021 2020 Restricted stock units and awards 20.4 2.4 10.5 Options to purchase shares of common stock 0.3 0.1 0.9 Co-Founder Grants 8.3 9.3 11.3 Convertible Senior Notes 37.8 31.9 — Warrants 37.8 31.9 — Total 104.6 75.6 22.7

Income Taxes

Income Taxes	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Income Taxes	Income Taxes For the years ended December 31, 2022, 2021, and 2020, the Company’s income (loss) from continuing operations before provision for income taxes was as follows: Year ended December 31, 2022 2021 2020 Domestic $ 37.8 $ 185.3 $ (57.7) Foreign 154.9 114.0 (192.5) Income (loss) before income taxes $ 192.7 $ 299.3 $ (250.2) The components of the benefit from (provision for) income taxes in the years ended December 31, 2022, 2021, and 2020, were as follows: Year ended December 31, 2022 2021 2020 Current: Federal $ (13.2) $ (0.4) $ — State (15.3) (0.7) (2.7) Foreign (7.5) (2.5) (6.0) Deferred: Federal 386.7 2.2 — State 30.0 0.4 — Foreign (20.2) 37.5 2.6 Benefit from (provision for) income taxes $ 360.5 $ 36.5 $ (6.1) A reconciliation of income taxes at the statutory federal income tax rate to the benefit from (provision for) income taxes included in the accompanying consolidated statements of operations is as follows: Year ended December 31, 2022 2021 2020 Tax (provision) benefit at federal statutory rate $ (40.5) $ (62.8) $ 52.5 State taxes, net of federal benefit (4.9) (5.5) 1.2 Foreign rate differential (34.0) 0.9 (12.2) Research and other credits 45.3 38.1 34.9 Non-deductible compensation (3.4) (6.2) (4.1) Permanent differences (1.8) (0.8) (1.8) Change in valuation allowance 409.9 51.4 (69.6) Stock-based compensation (4.3) 23.5 (3.2) Other non-deductible items (5.8) (2.1) (3.8) Benefit from (provision for) income taxes $ 360.5 $ 36.5 $ (6.1) The significant components of the Company’s deferred tax assets and liabilities as of December 31, 2022 and 2021 were as follows: As of December 31, 2022 2021 Deferred tax assets: Net operating loss carryforwards $ 40.8 $ 202.6 Research credit carryforwards 268.9 263.9 Stock-based compensation 24.1 25.2 Accruals and reserves 36.8 41.6 Lease liability 141.8 168.4 Convertible senior notes 47.5 57.3 Capitalized research expenditures 123.9 — Other 0.6 — Gross deferred tax assets 684.4 759.0 Valuation allowance (111.6) (586.7) Total deferred tax assets, net of valuation allowance 572.8 172.3 Deferred tax liabilities: Fixed assets and intangible assets 14.4 20.6 Right-of-use assets 59.5 110.2 Other 0.2 0.3 Total deferred tax liability 74.1 131.1 Net deferred tax assets $ 498.7 $ 41.2 As of December 31, 2022, the Company determined that U.S. federal and certain states deferred tax assets were more likely than not to be realized, resulting in a benefit from income taxes of $420.2 million as well as an adjustment recorded to additional paid in capital of $61.2 million. Accordingly, the valuation allowance recorded against deferred tax assets decreased by $475.1 million in the year ended December 31, 2022, compared to an increase of $3.0 million in the year ended December 31, 2021. Management applied judgment in assessing the positive and negative evidence available in the determination of the amount of deferred tax assets that were more-likely-than-not to be realized in the future. As of December 31, 2022, the Company maintained a valuation allowance against its California deferred tax assets. As of December 31, 2022, the Company had $13.3 million of federal, $118.5 million of state, and $150.3 million of foreign net operating loss carryforwards available to reduce future taxable income. Of the federal net operating loss carryforwards, $7.8 million will begin to expire in 2032 and $5.5 million will carryforward indefinitely, while state net operating losses begin to expire in 2035. The foreign net operating loss carryforwards will carryforward indefinitely. As of December 31, 2022, the Company had research credit carryforwards of $249.4 million and $150.3 million for federal and state income tax purposes, respectively, of which $72.5 million and $38.7 million is the unrecognized tax benefit portion related to the research credit carryforwards for federal and state, respectively. The federal credit carryforward will begin to expire in 2037. The state research credits have no expiration date. As of December 31, 2022, the Company had $0.5 million of foreign tax credit carryforwards, which will carryforward indefinitely. The Company also had $3.6 million of state enterprise zone credit carryforwards, which will begin to expire in 2023. Under Section 382 and 383 of the Internal Revenue Code of 1986, as amended, or the Code, if a corporation undergoes an “ownership change,” the corporation’s ability to use its pre-change net operating loss carryforwards and other pre-change attributes, such as research tax credits, to offset its post-change income may be limited. In general, an “ownership change” will occur if there is a cumulative change in our ownership by “5-percent shareholders” that exceeds 50 percentage points over a rolling three-year period. Similar rules may apply under state tax laws. The Company has determined that it has experienced multiple ownership changes and, as a result, the annual utilization of its net operating loss carryforwards and other pre-change attributes will be subject to limitation. However, the Company does not expect that the annual limitations will significantly impact its ability to utilize its net operating loss or tax credit carryforwards prior to expiration. As of December 31, 2022, the balance of unrecognized tax benefits was $127.2 million of which $88.5 million, if recognized, would affect the effective tax rate and $38.7 million would result in adjustment to deferred tax assets with corresponding adjustments to the valuation allowance. A reconciliation of the beginning and ending amount of unrecognized tax benefit is as follows: Year ended December 31, 2022 2021 2020 Balance of gross unrecognized tax benefits at the beginning of the fiscal year $ 107.3 $ 91.4 $ 74.5 Gross increases related to prior period tax positions — — 1.3 Gross decreases related to prior period tax positions — (0.3) — Gross increases related to current period tax positions 20.3 18.5 15.8 Reductions due to lapse in statute of limitations (0.4) (1.5) (0.2) Reductions due to settlements with taxing authorities — (0.8) — Balance of gross unrecognized tax benefits at the end of the fiscal year $ 127.2 $ 107.3 $ 91.4 The Company recognizes interest and/or penalties related to income tax matters as a component of income tax expense. As of December 31, 2022, the amount of accrued interest and penalties related to uncertain tax positions was $5.3 million. Interest and penalties recognized for the year ended December 31, 2022, 2021, and 2020 was $1.7 million, $0.4 million, and $0.7 million, respectively. It is reasonably possible that there could be changes to the amount of uncertain tax positions due to activities of the taxing authorities, settlement of audit issues, reassessment of existing uncertain tax positions, or the expiration of applicable statutes of limitations; however, the Company is not able to estimate the impact of these items at this time. The Company files income tax returns in the U.S. federal, multiple states, and foreign jurisdictions. All of the Company’s tax years from 2007 remain open for examination by the federal and state authorities, and from 2015 by foreign authorities.

Geographic Areas

Geographic Areas	12 Months Ended
	Dec. 31, 2022
Segment Reporting [Abstract]
Geographic Areas	Geographic Areas Long-lived assets The following table sets forth long-lived assets by geographic area: As of December 31, 2022 2021 United States $ 300.2 $ 316.6 International (1) 8.2 5.4 Total property and equipment, net $ 308.4 $ 322.0 (1) No single country other than the United States had a property and equipment balance greater than 10% of total property and equipment, net, as of December 31, 2022 and 2021. Revenue Revenue by geography is generally based on the address of the customer as defined in the Company’s subscription agreement. The following table sets forth revenue by geographic area for the years ended December 31, 2022, 2021, and 2020: Year ended December 31, 2022 2021 2020 United States $ 1,264.2 $ 1,130.0 $ 999.3 International (1) 1,060.7 1,027.9 914.6 Total revenue $ 2,324.9 $ 2,157.9 $ 1,913.9

Description of the Business a_2

Description of the Business and Summary of Significant Accounting Policies (Policies)	12 Months Ended
	Dec. 31, 2022
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Basis of presentation	The accompanying consolidated financial statements have been prepared in accordance with the United States of America generally accepted accounting principles (“GAAP”). The accompanying consolidated financial statements include the accounts of Dropbox and its wholly owned subsidiaries.
Basis of consolidation	All intercompany balances and transactions have been eliminated in consolidation.
Use of estimates	The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported and disclosed in the Company’s consolidated financial statements and accompanying notes. These estimates are based on information available as of the date of the consolidated financial statements. Management evaluates these estimates and assumptions on a regular basis. Actual results may differ materially from these estimates.The Company’s most significant estimates and judgments involve the valuation of right-of-use and other lease related assets and income taxes.
Financial information about segments and geographic areas	The Company manages its operations and allocates resources as a single operating segment. Further, the Company manages, monitors, and reports its financials as a single reporting segment. The Company’s chief operating decision-maker is its Chief Executive Officer, who reviews financial information presented on a consolidated basis for purposes of making operating decisions, assessing financial performance, and allocating resources. See Note 15, "Geographic Areas" for information regarding the Company’s long-lived assets and revenue by geography.
Foreign currency transactions	The assets and liabilities of the Company’s foreign subsidiaries are translated from their respective functional currencies into U.S. dollars at the exchange rates in effect at the balance sheet date. Revenue and expense amounts are translated at the average exchange rate for the period. Foreign currency translation gains and losses are recorded in other comprehensive (loss) income, net of tax.Gains and losses realized from foreign currency transactions (those transactions denominated in currencies other than the foreign subsidiaries’ functional currency) are included in other income, net. Monetary assets and liabilities are remeasured using foreign currency exchange rates at the end of the period, and non-monetary assets are remeasured based on historical exchange rates.
Revenue recognition, Cost of revenue, and Deferred commissions, net	The Company derives its revenue from subscription fees from customers for access to its platform. The Company’s policy is to exclude sales and other indirect taxes when measuring the transaction price of its subscription agreements. The Company accounts for revenue contracts with customers through the following steps: • Identification of the contract, or contracts, with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract • Recognition of revenue when, or as, the Company satisfies a performance obligation The Company’s subscription agreements generally have monthly or annual contractual terms and a small percentage have multi-year contractual terms. Revenue is recognized ratably over the related contractual term beginning on the date that the platform is made available to a customer. Access to the platform represents a series of distinct services as the Company continually provides access to, and fulfills its obligation to, the end customer over the subscription term. The series of distinct services represents a single performance obligation that is satisfied over time. The Company recognizes revenue ratably because the customer receives and consumes the benefits of the platform throughout the contract period. The Company’s contracts are generally non-cancelable. The Company bills in advance for monthly contracts and typically bills annually in advance for contracts with terms of one year or longer. The Company also recognizes an immaterial amount of contract assets, or unbilled receivables, primarily relating to consideration for services completed but not billed at the reporting date. Unbilled receivables are classified as receivables when the Company has the right to invoice the customer. The Company records contract liabilities when cash payments are received or due in advance of performance to deferred revenue. Deferred revenue primarily relates to the advance consideration received from the customer. The price of subscriptions is generally fixed at contract inception and therefore, the Company’s contracts do not contain a significant amount of variable consideration. As a result, the amount of revenue recognized in the periods presented from performance obligations satisfied (or partially satisfied) in previous periods was not material.
Stock-based compensation	The Company has primarily granted restricted stock units (“RSUs”) to its employees and members of the Board of Directors under the 2008 Equity Incentive Plan (“2008 Plan”), the 2017 Equity Incentive Plan (“2017 Plan”), and the 2018 Equity Incentive Plan (“2018 Plan” and together with the 2008 Plan and 2017 Plan, the "Dropbox Equity Incentive Plans”). Since August 2015, the Company has granted RSUs, which have a service based vesting condition over a four-year period vesting quarterly, as the only stock-based payment awards to its employees, with the exception of awards granted to its co-founder and certain executives, and has not granted any stock options to employees under the Dropbox Equity Incentive Plans. The Company recognizes compensation expense associated with RSUs on a straight-line basis over the requisite service period and accounts for forfeitures in the period in which they occur. The Board of Directors determines the fair value of each share of underlying common stock based on the closing price of the Company's Class A common stock as reported on the Nasdaq Global Select Market on the date of the grant. In March 2021, in connection with the acquisition of DocSend, Inc. (“DocSend”), the Company assumed unvested stock options and an immaterial number of unvested RSUs that had been granted under DocSend's 2013 Stock Plan and DocSend's 2015 Stock Option and Grant Plan. The fair value of the DocSend options assumed were based upon the Black-Scholes option-pricing model. See Note 12 "Stockholders' (Deficit) Equity" for further information.
Advertising and promotional expense	Advertising and promotional expenses are primarily included in sales and marketing expenses within the consolidated statements of operations and are expensed when incurred. Advertising and promotional expenses were $94.8 million, $108.6 million, and $81.4 million during the years ended December 31, 2022, 2021, and 2020, respectively.
Cash and cash equivalents	Cash consists primarily of cash on deposit with banks and includes amounts in transit from payment processors for credit and debit card transactions, which typically settle within five business days. Cash equivalents include highly liquid investments purchased with an original maturity date of 90 days or less from the date of purchase.The Company monitors its credit risk by considering factors such as historical experience, credit ratings, current economic conditions, and reasonable and supportable forecasts.
Short-term investments	The Company’s short-term investments are primarily comprised of corporate notes and obligations, U.S. Treasury securities, certificates of deposit, asset-backed securities, commercial paper, U.S. agency obligations, foreign government securities, supranational securities, and municipal securities. The Company determines the appropriate classification of its short-term investments at the time of purchase and reevaluates such designation at each balance sheet date. The Company has classified and accounted for its short-term investments as available-for-sale securities as the Company may sell these securities at any time for use in its current operations or for other purposes, even prior to maturity. As a result, the Company classifies its short-term investments, including securities with stated maturities beyond twelve months, within current assets in the consolidated balance sheets. The Company's short-term investments are recorded at fair value each reporting period. Unrealized gains and losses on these short-term investments are reported as a separate component of accumulated other comprehensive loss in the consolidated balance sheets until realized. Unrealized gains and losses for any short-term investments that management intends to sell or it is more likely than not that management will be required to sell prior to their anticipated recovery are recorded in other income, net. The Company segments its portfolio based on the underlying risk profiles of the securities and has a zero-loss expectation
Concentrations of credit risk	Financial instruments that potentially subject the Company to significant concentrations of credit risk consist primarily of cash, cash equivalents, accounts receivable, and short-term investments. The Company places its cash and cash equivalents, and short-term investments with well-established financial institutions. Trade accounts receivable are typically unsecured and are derived from revenue earned from customers located around the world.
Trade and other receivables, net and Non-trade receivables	Trade and other receivables, net Trade and other receivables, net consists primarily of trade receivables that are recorded at the invoice amount, net of an allowance for expected credit losses. The allowance for expected credit losses is based on the Company’s assessment of the collectability of accounts receivable. The Company assesses collectability by reviewing accounts receivable on a collective basis where similar characteristics exist and on an individual basis when the Company identifies specific customers with known disputes or collectability issues. The Company regularly reviews the adequacy of the allowance for expected credit losses by considering the age of each outstanding invoice, the collection history of each customer, and other relevant factors, including contractual term and current and future economic conditions. The Company's allowance for expected credit losses was $0.7 million and $1.0 million as of December 31, 2022 and 2021, respectively. Non-trade receivables
Property and equipment, net	Equipment is stated at cost less accumulated depreciation. Depreciation is computed using the straight-line method over the estimated useful life of the related asset, which is generally three The following table presents the estimated useful lives of property and equipment: Property and equipment Useful life Buildings 20 to 30 years Datacenter and other computer equipment 3 to 5 years Office equipment and other 3 to 7 years Leasehold improvements Lesser of estimated useful life or remaining lease term
Lease obligations	The Company leases office space, datacenters, and equipment under non-cancelable finance and operating leases with various expiration dates through 2036. The Company determines if an arrangement contains a lease at inception. Operating lease right-of-use assets and lease liabilities are recognized at the present value of the future lease payments at commencement date. The interest rate implicit in the Company’s operating leases is not readily determinable, and therefore an incremental borrowing rate is estimated to determine the present value of future payments. The estimated incremental borrowing rate factors in a hypothetical interest rate on a collateralized basis with similar terms, payments, and economic environments. Operating lease right-of-use assets also include any prepaid lease payments and lease incentives. Certain of the operating lease agreements contain rent concession, rent escalation, and option to renew provisions. Rent concession and rent escalation provisions are considered in determining the single lease cost to be recorded over the lease term. Single lease cost is recognized on a straight-line basis over the lease term commencing on the date the Company has the right to use the leased property. The lease terms may include options to extend or terminate the lease. The Company generally uses the base, non-cancelable, lease term when recognizing the lease assets and liabilities, unless it is reasonably certain that the option will be exercised. In addition, certain operating lease agreements contain tenant improvement allowances from its landlords. These allowances are accounted for as lease incentives and decrease the Company's right-of-use asset and reduce single lease cost over the lease term. As part of the Company's Virtual First strategy, Dropbox has retained a portion of its office space for in-person collaboration while the remainder will be subleased. During the year ended December 31, 2022, the Company recorded impairment charges of $175.2 million related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted its subleasing strategy in conjunction with its shift to Virtual First. During the year ended December 31, 2021, the Company recorded an impairment charge of $31.3 million related to its operating leases and related real estate assets, and assets acquired as part of the acquisition of DocSend in the first quarter of 2021. These impairment charges were recorded as a result of adverse changes in the corporate real estate market which impacted its subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information. The Company leases certain equipment from various third parties, through equipment finance leases. These leases either include a bargain purchase option, a full transfer of ownership at the completion of the lease term, or the terms of the leases are at least 75 percent of the useful lives of the assets and are therefore classified as finance leases. These leases are capitalized in property and equipment, net and the related amortization of assets under finance leases is included in depreciation and amortization expense in the Company’s consolidated statements of operations. Initial asset values and finance lease obligations are based on the present value of future minimum lease payments.
Internal use software	The Company capitalizes certain costs related to developed or modified software solely for its internal use and cloud based applications used to deliver its platform. The Company capitalizes costs during the application development stage once the preliminary project stage is complete, management authorizes and commits to funding the project, and it is probable that the project will be completed and that the software will be used to perform the function intended. Costs related to preliminary project activities and post implementation activities are expensed as incurred. Capitalized internal use software costs were not material to the Company’s consolidated financial statements during the years ended December 31, 2022, 2021, and 2020.
Business combinations	The Company uses best estimates and assumptions, including but not limited to, future expected cash flows, expected asset lives, and discount rates, to assign a fair value to the tangible and intangible assets acquired and liabilities assumed in business combinations as of the acquisition date. These estimates are inherently uncertain and subject to refinement. During the measurement period, which may be up to one year from the acquisition date, adjustments to the fair value of these tangible and intangible assets acquired and liabilities assumed may be recorded, with the corresponding offset to goodwill. Upon the conclusion of the measurement period or final determination of the fair value of assets acquired or liabilities assumed, whichever comes first, any subsequent adjustments are recorded to the Company’s consolidated statements of operations.
Long-lived assets, including goodwill and other acquired intangible assets, net	The Company evaluates the recoverability of its property and equipment and finite-lived intangible assets for possible impairment whenever events or circumstances indicate that the carrying amount of such assets may not be recoverable. The evaluation is performed at the lowest level for which identifiable cash flows are largely independent of the cash flows of other assets and liabilities. Recoverability of these assets is measured by a comparison of the carrying amounts to the future undiscounted cash flows the assets are expected to generate. If such review determines that the carrying amount of specific property and equipment or intangible assets is not recoverable, the carrying amount of such assets is reduced to its fair value. The Company reviews goodwill for impairment at least annually in the fourth quarter, or more frequently if events or changes in circumstances would more likely than not reduce the fair value of its single reporting unit below its carrying value. At December 31, 2022, the single reporting unit had a zero or negative carrying value of net assets. Goodwill allocated to the single reporting unit is $403.3 million at December 31, 2022. The Company has not recorded impairment charges on goodwill or intangible assets for the periods presented in these consolidated financial statements. The Company recorded impairment charges of $175.2 million and $31.3 million related to real estate assets and other lease related obligations during the years ended December 31, 2022 and 2021, respectively, in conjunction with its decision to move towards a Virtual First work model. See Note 9 "Leases" for further information. Acquired property and equipment and finite-lived intangible assets are amortized over their useful lives. The Company evaluates the estimated remaining useful life of these assets when events or changes in circumstances warrant a revision to the remaining period of amortization. If the Company revises the estimated useful life assumption for any asset, the remaining unamortized balance is amortized or depreciated over the revised estimated useful life on a prospective basis.
Income taxes	Deferred income tax balances reflect the effects of temporary differences between the financial reporting and tax bases of the Company’s assets and liabilities using enacted tax rates expected to apply when taxes are actually paid or recovered. In addition, deferred tax assets are recorded for net operating loss and credit carryforwards. A valuation allowance is provided against deferred tax assets unless it is more likely than not that they will be realized based on all available positive and negative evidence. Such evidence includes, but is not limited to, recent cumulative earnings or losses, expectations of future taxable income by taxing jurisdiction, and the carry-forward periods available for the utilization of deferred tax assets. As of December 31, 2022, the Company determined that all of its deferred tax assets related to federal and certain states are more likely than not to be realized, resulting in a benefit to income taxes of $420.2 million from the release of the valuation allowance. As of December 31, 2021, the Company released the valuation allowance on its Irish deferred tax assets resulting in an income tax benefit of $38.1 million. The Company uses a two-step approach to recognizing and measuring uncertain income tax positions. The first step is to evaluate the tax position for recognition by determining if the weight of available evidence indicates it is more likely than not that the position will be sustained on audit. The second step is to measure the tax benefit as the largest amount, which is more than 50% likely of being realized upon ultimate settlement. The Company recognizes interest and penalties related to unrecognized tax benefits as income tax expense. Although the Company believes that it has adequately reserved for its uncertain tax positions, it can provide no assurance that the final tax outcome of these matters will not be materially different. The Company evaluates its uncertain tax positions on a regular basis and evaluations are based on a number of factors, including changes in facts and circumstances, changes in tax law, correspondence with tax authorities during the course of an audit, and effective settlement of audit issues. To the extent that the final tax outcome of these matters is different than the amounts recorded, such differences will affect the provision for income taxes in the period in which such determination is made and could have a material impact on the Company’s financial condition and results of operations.
Fair value measurement	The Company applies fair value accounting for all financial assets and liabilities and non-financial assets and liabilities that are recognized or disclosed at fair value in the financial statements on a recurring basis. The Company defines fair value as the price that would be received from selling an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. When determining fair value measurements for assets and liabilities, the Company considers the principal or most advantageous market in which it would transact and the market-based risk measurements or assumptions that market participants would use in pricing the asset or liability, such as risks inherent in valuation techniques, transfer restrictions, and credit risk. Fair value is estimated by applying the following hierarchy, which prioritizes the inputs used to measure fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available and significant to the fair value measurement: Level 1 —Quoted prices in active markets for identical assets or liabilities. Level 2 —Observable inputs other than quoted prices in active markets for identical assets and liabilities, quoted prices for identical or similar assets or liabilities in inactive markets, or other inputs that are observable or can be corroborated by observable market data for substantially the full term of the assets or liabilities. Level 3 —Inputs that are generally unobservable and typically reflect management’s estimate of assumptions that market participants would use in pricing the asset or liability.
Recently issued accounting pronouncements not yet adopted and accounting pronouncements	Recently issued accounting pronouncements not yet adopted In March 2022, the FASB issued ASU 2022-02, Financial Instruments—Credit Losses (Topic 326): Troubled Debt Restructurings and Vintage Disclosures , which eliminates the accounting guidance on troubled debt restructurings for creditors in ASC 310-40 and amends the guidance on "vintage disclosures" to require disclosure of current-period gross write-offs by year of origination. The ASU also updates the requirements related to accounting for credit losses under ASC 326 and adds enhanced disclosures for creditors with respect to loan refinancings and restructurings for borrowers experiencing financial difficulty. The amendments in ASU 2022-02 are effective for fiscal years beginning after December 15, 2022, and interim periods within those fiscal years. The Company does not expect the adoption of ASU 2022-02 to have a significant impact on its consolidated financial statements. Recently adopted accounting pronouncements In May 2021, the FASB issued ASU 2021-04, Earnings Per Share (Topic 260), Debt - Modifications and Extinguishments (Subtopic 470-50), Compensation - Stock Compensation (Topic 718), and Derivatives and Hedging - Contracts in Entity's Own Equity (Subtopic 815-40) to clarify and reduce diversity in an issuer’s accounting for modifications or exchanges of freestanding equity-classified written call options (for example, warrants) that remain equity classified after modification or exchange. The Company adopted ASU 2021-04 on January 1, 2022. The adoption of the standard did not have a material impact on the Company's consolidated financial statements. In July 2021, the FASB issued ASU 2021-05, Leases (Topic 842) , which amends ASC 842 so that lessors are no longer required to recognize a selling loss upon commencement of a lease with variable lease payments that, prior to the amendments, would have been classified as a sales-type or direct financing lease. Furthermore, a lessor must classify as an operating lease any lease that would otherwise be classified as a sales-type or direct financing lease and that would result in the recognition of a selling loss at lease commencement, provided that the lease includes variable lease payments that do not depend on an index or rate. The Company adopted ASU 2021-05 on January 1, 2022. The adoption of the standard did not have a material impact on the Company's consolidated financial statements. In October 2021, the FASB issued ASU 2021-08, Business Combinations (Topic 805): Accounting for Contract Assets and Contract Liabilities from Contracts with Customers , which requires entities to recognize and measure contract assets and contract liabilities acquired in a business combination in accordance with Topic 606, Revenue from Contracts with Customers, instead of fair value at the acquisition date in accordance with Topic 805. The amendments in ASU 2021-08 results in the acquirer recording acquired contract assets and liabilities on the same basis as they would have been recorded by the acquiree before the acquisition under ASC Topic 606. The amendments in ASU 2021-08 are effective for fiscal years beginning after December 15, 2022, but early adoption is permitted, including in an interim period. The Company adopted this guidance in the fourth quarter of 2022 on a prospective basis. The adoption of this standard did not have a material impact on our consolidated financial statements.
Goodwill	Goodwill represents the excess of the purchase price in a business combination over the fair value of net tangible and intangible assets acquired.Goodwill amounts are not amortized but tested for impairment on an annual basis.
Net income (loss) per share	The Company computes net income (loss) per share using the two-class method required for multiple classes of common stock and participating securities. The rights, including the liquidation and dividend rights, of the Class A common stock and Class B common stock are substantially identical, other than voting rights. Accordingly, the Class A common stock and Class B common stock share equally in the Company’s net income and losses.

Description of the Business a_3

Description of the Business and Summary of Significant Accounting Policies (Tables)	12 Months Ended
	Dec. 31, 2022
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Schedule of Estimated Useful Lives of Property and Equipment	The following table presents the estimated useful lives of property and equipment: Property and equipment Useful life Buildings 20 to 30 years Datacenter and other computer equipment 3 to 5 years Office equipment and other 3 to 7 years Leasehold improvements Lesser of estimated useful life or remaining lease term Property and equipment, net consisted of the following: As of December 31, 2022 2021 Datacenter and other computer equipment $ 671.3 $ 634.5 Furniture and fixtures 19.8 21.7 Leasehold improvements 118.0 106.7 Construction in progress 2.8 11.7 Total property and equipment 811.9 774.6 Accumulated depreciation and amortization (503.5) (452.6) Property and equipment, net $ 308.4 $ 322.0

Cash, Cash Equivalents and Sh_2

Cash, Cash Equivalents and Short-Term Investments (Tables)	12 Months Ended
	Dec. 31, 2022
Cash and Cash Equivalents [Abstract]
Schedule of Cash, Cash Equivalents and Short-Term Investments	The amortized cost, unrealized gains and losses and estimated fair value of the Company's cash, cash equivalents and short-term investments as of December 31, 2022 consisted of the following: Amortized cost Unrealized gain Unrealized loss Estimated fair value Cash $ 90.1 $ — $ — $ 90.1 Cash equivalents Money market funds 139.5 — — 139.5 Commercial paper 3.2 — — 3.2 Total cash & cash equivalents $ 232.8 $ — $ — $ 232.8 Short-term investments Corporate notes and obligations 512.1 0.1 (22.7) 489.5 U.S. Treasury securities 360.2 0.2 (14.0) 346.4 Asset backed securities 117.6 — (6.0) 111.6 Municipal securities 65.3 — (4.1) 61.2 Commercial paper 46.4 — — 46.4 Certificates of deposit 29.1 — — 29.1 U.S. agency obligations 18.4 — (0.8) 17.6 Foreign government obligations 6.0 — (0.4) 5.6 Supranational securities 3.4 — (0.2) 3.2 Total short-term investments 1,158.5 0.3 (48.2) 1,110.6 Total $ 1,391.3 $ 0.3 $ (48.2) $ 1,343.4 The amortized cost, unrealized gains and losses and estimated fair value of the Company's cash, cash equivalents and short-term investments as of December 31, 2021 consisted of the following: Amortized cost Unrealized gain Unrealized loss Estimated fair value Cash $ 142.7 $ — $ — $ 142.7 Cash equivalents Money market funds 390.3 — — 390.3 Total cash and cash equivalents $ 533.0 $ — $ — $ 533.0 Short-term investments Corporate notes and obligations 607.4 0.4 (4.0) 603.8 U.S. Treasury securities 240.4 — (2.9) 237.5 Asset backed securities 140.7 0.1 (1.2) 139.6 Municipal securities 70.5 — (0.7) 69.8 U.S. agency obligations 14.6 — (0.2) 14.4 Commercial paper 61.7 — — 61.7 Supranational Securities 8.0 — (0.1) 7.9 Foreign government obligations 18.4 — (0.1) 18.3 Certificates of deposit 32.1 — — 32.1 Total short-term investments 1,193.8 0.5 (9.2) 1,185.1 Total $ 1,726.8 $ 0.5 $ (9.2) $ 1,718.1
Contractual Maturities of Short Term Investments	The following table presents the contractual maturities of the Company’s short-term investments as of December 31, 2022: Amortized cost Estimated fair value Due within one year $ 398.6 $ 393.5 Due between one to three years 556.8 531.8 Due after three years 203.1 185.3 Total $ 1,158.5 $ 1,110.6
Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value	The following tables present the breakdown of the short-term investments that have been in a continuous unrealized loss position aggregated by investment category, as of December 31, 2022 and December 31, 2021: As of December 31, 2022 Less than 12 months More than 12 months Total Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Corporate notes and obligations $ 176.5 $ (3.5) $ 292.3 $ (19.2) $ 468.8 $ (22.7) U.S. Treasury securities 110.9 (1.8) 176.9 (12.2) 287.8 (14.0) Asset backed securities 13.7 (0.4) 90.4 (5.6) 104.1 (6.0) Municipal securities 9.3 (0.3) 51.6 (3.8) 60.9 (4.1) U.S. agency obligations 3.9 — 13.8 (0.8) 17.7 (0.8) Foreign government obligations — — 5.5 (0.4) 5.5 (0.4) Supranational securities — — 3.2 (0.2) 3.2 (0.2) Total $ 314.3 $ (6.0) $ 633.7 $ (42.2) $ 948.0 $ (48.2) As of December 31, 2021 Less than 12 months More than 12 months Total Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Corporate notes and obligations $ 498.6 $ (4.0) $ — $ — $ 498.6 $ (4.0) U.S. Treasury securities 218.0 (2.9) — — 218.0 (2.9) Asset backed securities 120.7 (1.2) — — 120.7 (1.2) Municipal securities 66.0 (0.7) — — 66.0 (0.7) U.S. agency obligations 14.4 (0.2) — — 14.4 (0.2) Foreign government obligations 15.4 (0.1) — — 15.4 (0.1) Supranational securities 7.9 (0.1) — — 7.9 (0.1) Total $ 941.0 $ (9.2) $ — $ — $ 941.0 $ (9.2)

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Schedule of Financial Instruments Measured at Fair Value on Recurring Basis	The following table presents information about the Company’s financial instruments that are measured at fair value on a recurring basis using the input categories discussed in Note 1: As of December 31, 2022 Level 1 Level 2 Level 3 Total Cash equivalents Money market funds $ 139.5 $ — $ — $ 139.5 Commercial paper — 3.2 — $ 3.2 Total cash equivalents 139.5 3.2 — 142.7 Short-term investments Corporate notes and obligations — 489.5 — 489.5 U.S. Treasury securities — 346.4 — 346.4 Asset backed securities — 111.6 — 111.6 Municipal securities — 61.2 — 61.2 Commercial paper — 46.4 — 46.4 Certificates of deposit — 29.1 — 29.1 Foreign government obligations — 5.6 — 5.6 U.S. agency obligations — 17.6 — 17.6 Supranational securities — 3.2 — 3.2 Total short-term investments — 1,110.6 — 1,110.6 Total $ 139.5 $ 1,113.8 $ — $ 1,253.3 As of December 31, 2021 Level 1 Level 2 Level 3 Total Cash equivalents Money market funds $ 390.3 $ — $ — $ 390.3 Total Cash Equivalents $ 390.3 $ — $ — $ 390.3 Short-term investments Corporate notes and obligations — 603.8 — 603.8 U.S. Treasury securities — 237.5 — 237.5 Asset backed securities — 139.6 — 139.6 Municipal securities — 69.8 — 69.8 U.S. agency obligations — 14.4 — 14.4 Commercial paper — 61.7 — 61.7 Supranational securities — 7.9 — 7.9 Foreign government obligations — 18.3 — 18.3 Certificates of deposit — 32.1 — 32.1 Total short-term investments — 1,185.1 — 1,185.1 Total $ 390.3 $ 1,185.1 $ — $ 1,575.4

Property and Equipment, Net (Ta

Property and Equipment, Net (Tables)	12 Months Ended
	Dec. 31, 2022
Property, Plant and Equipment [Abstract]
Schedule of Property and Equipment, Net	The following table presents the estimated useful lives of property and equipment: Property and equipment Useful life Buildings 20 to 30 years Datacenter and other computer equipment 3 to 5 years Office equipment and other 3 to 7 years Leasehold improvements Lesser of estimated useful life or remaining lease term Property and equipment, net consisted of the following: As of December 31, 2022 2021 Datacenter and other computer equipment $ 671.3 $ 634.5 Furniture and fixtures 19.8 21.7 Leasehold improvements 118.0 106.7 Construction in progress 2.8 11.7 Total property and equipment 811.9 774.6 Accumulated depreciation and amortization (503.5) (452.6) Property and equipment, net $ 308.4 $ 322.0

Business Combinations (Tables)

Business Combinations (Tables)	12 Months Ended
	Dec. 31, 2022
Business Combination and Asset Acquisition [Abstract]
Schedule of Purchase Consideration Transferred	The purchase consideration transferred consisted of the following: Purchase consideration Cash paid to stockholders $ 50.0 Cash paid for extinguishing shadow stock units 3.2 Transaction costs paid by Dropbox on behalf of FormSwift 2.0 Cash purchase consideration $ 55.2 Indemnification holdback (1) 14.3 Total purchase consideration $ 69.5 (1) Approximately $14.3 million of the total purchase consideration was withheld as an indemnification holdback to be used for the purpose of satisfying any indemnification claims made by the Company for a period of 18 months following the transaction close date. Any remaining indemnity will be released to the seller's representative following the 18 month period. The purchase consideration transferred consisted of the following: Purchase consideration Cash paid to common and preferred stockholders and vested option holders $ 125.5 Transaction costs paid by Dropbox on behalf of DocSend 5.0 Fair value of assumed DocSend options attributable to pre-combination services (1) 1.2 Purchase price adjustments 0.1 Total purchase consideration $ 131.8 (1) The fair value of options assumed was based upon the Black-Scholes option-pricing model.
Schedule of Recognized Identified Assets Acquired and Liabilities Assumed	The purchase consideration was allocated to the tangible and intangible assets and liabilities acquired as of the acquisition date, with the excess recorded to goodwill as shown below. The fair value of assets and liabilities acquired may change as additional information is received during the measurement period. The measurement period will end no later than one-year from the acquisition date. Assets acquired: Cash and cash equivalents $ 0.4 Acquisition-related intangible assets 41.2 Accounts receivable, prepaid and other assets 3.4 Total assets acquired $ 45.0 Liabilities assumed: Accounts payable, accrued and other liabilities $ 4.6 Deferred revenue 6.6 Total liabilities assumed 11.2 Net assets acquired, excluding goodwill 33.8 Total purchase consideration 69.5 Goodwill (2) $ 35.7 (2) The goodwill recognized was primarily attributable to the opportunity to expand the user base of the Company's platform. A portion of the goodwill is deductible for U.S. federal income tax purposes. Assets acquired: Cash and cash equivalents $ 5.1 Acquisition-related intangible assets 20.6 Accounts receivable, prepaid and other assets 6.1 Total assets acquired $ 31.8 Liabilities assumed: Accounts payable, accrued and other liabilities $ 6.4 Deferred revenue 1.9 Deferred tax liability 1.9 Total liabilities assumed 10.2 Net assets acquired, excluding goodwill 21.6 Total purchase consideration 131.8 Goodwill (2) $ 110.2 (2) The goodwill recognized was primarily attributable to the opportunity to expand the user base of the Company's platform. The goodwill is not deductible for U.S. federal income tax purposes.
Schedule of Identifiable Finite-lived Intangible Assets Acquired and Estimated Weighted Average Useful Lives	The fair value of the separately identifiable finite-lived intangible assets acquired and estimated weighted average useful lives are as follows: Estimated fair values Estimated weighted average useful lives Developed technology $ 24.2 5.0 Customer relationships 16.4 2.0 Trade name 0.6 1.0 Total acquisition-related intangible assets $ 41.2 The fair value of the separately identifiable finite-lived intangible assets acquired and estimated weighted average useful lives are as follows: Estimated fair values Estimated weighted average useful lives Developed technology $ 11.5 5.0 Customer relationships 8.1 5.0 Trade name 1.0 5.0 Total acquisition-related intangible assets $ 20.6

Intangible Assets (Tables)

Intangible Assets (Tables)	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of Intangible Assets	Intangible assets consisted of the following: As of December 31, Weighted- (In years) 2022 2021 Developed technology $ 74.3 $ 45.9 4.2 Customer relationships 43.2 28.6 2.2 Patents 19.4 19.5 4.3 Software 8.9 9.0 0.7 Trademarks and trade names 5.8 5.6 1.6 Licenses 4.6 4.6 0.0 Assembled workforce in asset acquisitions 3.4 3.0 3.3 Other 1.1 0.8 2.8 Total intangibles 160.7 117.0 Accumulated amortization (72.4) (63.4) Intangible assets, net $ 88.3 $ 53.6
Schedule of Expected Future Amortization Expense	Expected future amortization expense for intangible assets as of December 31, 2022, is as follows: 2023 $ 30.4 2024 25.1 2025 14.8 2026 10.4 2027 7.0 Thereafter 0.6 Total $ 88.3

Goodwill (Tables)

Goodwill (Tables)	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of Changes in Carrying Amounts of Goodwill	The changes in the carrying amounts of goodwill were as follows: Balance at December 31, 2021 $ 356.6 FormSwift acquisition 35.7 Other acquisition 14.4 Effect of foreign currency translation (3.4) Balance at December 31, 2022 $ 403.3

Debt (Tables)

Debt (Tables)	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Schedule of Convertible Debt	The following is a summary of the Company’s convertible senior notes as of December 31, 2022 and December 31, 2021. 2026 Notes 2028 Notes Total December 31, 2022 Principal balance $ 695.8 $ 693.3 $ 1,389.1 Unamortized issuance costs (7.0) (8.1) (15.1) Carrying value, net $ 688.8 $ 685.2 $ 1,374.0 December 31, 2021 Principal balance $ 695.8 $ 693.3 $ 1,389.1 Unamortized issuance costs (9.1) (9.7) (18.8) Carrying value, net $ 686.7 $ 683.6 $ 1,370.3
Schedule of Maturities of Long-term Debt	Maturities on the Company's long-term convertible debt are as follows: Convertible Debt 2023 $ — 2024 — 2025 — 2026 695.8 2027 — Thereafter 693.3 Total 1,389.1

Leases (Tables)

Leases (Tables)	12 Months Ended
	Dec. 31, 2022
Leases [Abstract]
Components of Single Lease Cost and Other Information	The components of lease cost were as follows: Year ended December 31, 2022 2021 Operating lease cost (1) $ 91.7 $ 107.8 Finance lease cost: Amortization of assets under finance lease 111.4 107.1 Interest 7.5 8.8 Total finance lease cost $ 118.9 $ 115.9 (1) Is presented gross of sublease income and includes short-term leases, which are immaterial. Other information related to leases was as follows: Year ended December 31, 2022 Year ended December 31, 2021 Supplemental Cash Flow Information: Cash paid for amounts included in the measurement of lease liabilities: Payments for operating leases included in cash from operating activities $ 104.7 $ 130.3 Payments for finance leases included in cash from operating activities 7.5 8.8 Payments for finance leases included in cash from financing activities 127.5 110.4 Assets obtained in exchange for lease obligations: Operating leases 33.0 67.1 Finance leases $ 105.8 $ 127.3 As of December 31, 2022 As of December 31, 2021 Weighted Average Remaining Lease Term (in years) Operating leases 9.9 10.2 Finance leases 2.6 2.7 Weighted Average Discount Rate Operating leases 4.1 % 4.0 % Finance leases 3.4 % 2.9 %
Maturities of Operating Lease Liabilities	Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details.
Maturities of Finance Lease Liabilities	Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details.
Payment to be Received on Operating Leases to Subtenants	Future non-cancelable rent payments from the Company's subtenants as of December 31, 2022 were as follows: Year ending December 31, Operating leases 2023 17.5 2024 16.7 2025 15.6 2026 11.9 2027 8.2 Thereafter 26.4 Total future sublease rent payments 96.3 Less subtenant incentive (1.1) Total future sublease rent payments, net $ 95.2

Commitments and Contingencies (

Commitments and Contingencies (Tables)	12 Months Ended
	Dec. 31, 2022
Commitments and Contingencies Disclosure [Abstract]
Schedule of Other Commitments	Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details.
Maturities of Finance Lease Liabilities	Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details.
Maturities of Operating Lease Liabilities	Future minimum lease payments under non-cancellable leases as of December 31, 2022 were as follows: Year ending December 31, Operating leases (1) Finance leases 2023 $ 94.7 $ 121.9 2024 89.9 87.4 2025 84.5 49.4 2026 64.9 21.1 2027 65.1 0.2 Thereafter 411.7 — Total future minimum lease payments 810.8 280.0 Less imputed interest (155.5) (13.5) Less tenant improvement receivables (1.2) — Total liability $ 654.1 $ 266.5 (1) Consists of future non-cancelable minimum rental payments under operating leases for the Company’s corporate offices and datacenters where the Company has possession, excluding rent payments for short-term lease obligations, payments from the Company’s subtenants and variable operating expenses. Future minimum payments under the Company's non-cancelable leases, finance lease obligations, and other commitments as of December 31, 2022, are as follows, and exclude non-cancelable rent payments from the Company's subtenants: Finance Operating lease commitments (1) Other commitments (2) Year ended December 31: 2023 121.9 94.7 43.6 2024 87.4 89.9 4.1 2025 49.4 84.5 1.1 2026 21.1 64.9 0.4 2027 0.2 65.1 — Thereafter — 411.7 17.6 Future minimum payments 280.0 810.8 66.8 Less interest and taxes (13.5) Less current portion of the present value of minimum lease payments (114.8) Financing lease obligations, net of current portion 151.7 (1) This balance includes short-term lease obligations. (2) This balance excludes indemnification and founder holdbacks related to our acquisitions. See Note 5, "Business Combinations" for further details.

Accrued and Other Current Lia_2

Accrued and Other Current Liabilities (Tables)	12 Months Ended
	Dec. 31, 2022
Payables and Accruals [Abstract]
Schedule of Accrued and Other Current Liabilities	Accrued and other current liabilities consisted of the following: As of December 31, 2022 2021 Non-income taxes payable $ 76.4 $ 77.4 Accrued legal and other external fees 25.5 24.0 Other accrued and current liabilities 38.0 39.4 Total accrued and other current liabilities $ 139.9 $ 140.8

Stockholders_ (Deficit) Equity

Stockholders’ (Deficit) Equity (Tables)	12 Months Ended
	Dec. 31, 2022
Stockholders' Equity Note [Abstract]
Schedule of Stock Option and Restricted Stock Activity	Stock option and restricted stock activity for the Plans was as follows for the years ended December 31, 2022 and 2021: Options outstanding Restricted stock Number of Number of Weighted- Weighted- Aggregate Intrinsic Value Number of Weighted- Balance as of December 31, 2020 78.5 1.3 $ 13.73 5.7 $ 11.4 31.9 $ 19.79 Additional shares authorized 20.3 Stock options assumed (1) 0.4 0.4 $ 2.17 Options exercised and restricted stock units and awards released (0.7) 9.77 (12.7) 20.77 Options and restricted stock units and awards canceled 11.0 (0.1) 11.84 (11.0) 21.12 Shares withheld related to net share settlement of restricted stock units and awards 4.6 20.71 Options and restricted stock units and awards granted (19.6) 19.6 26.34 Balance as of December 31, 2021 95.2 0.9 $ 12.09 5.4 $ 10.0 27.8 $ 24.17 Additional shares authorized 18.8 Options exercised and restricted stock units and awards released (0.1) 3.00 (14.3) 23.37 Options and restricted stock units and awards canceled 6.9 (0.4) 18.53 (6.5) 23.72 Shares withheld related to net share settlement of restricted stock units and awards 5.1 23.40 Options and restricted stock units and awards granted (27.8) 27.8 22.68 Balance as of December 31, 2022 98.2 0.4 $ 11.30 4.5 $ 4.5 34.8 $ 23.40 Vested at December 31, 2022 0.3 $ 13.83 4.1 $ 2.8 — $ — Unvested at December 31, 2022 0.1 $ 2.01 $ 1.7 34.8 $ 23.40 (1) This amount includes an immaterial amount of unvested RSUs that were assumed as part of the acquisition of DocSend. The RSUs had a weighted-average grant date fair value of $26.86 per share and a total fair value of $0.4 million, all of which will be recognized as post-combination stock-based compensation expense.
Schedule of Pre-Tax Intrinsic Value of Options Exercised	The following table summarizes information about the pre-tax intrinsic value of options exercised during the years ended December 31, 2022 and 2021: Year ended 2022 2021 Intrinsic value of options exercised $ 2.9 $ 12.3
Fair Value of Stock Options Assumptions Used	The fair value of stock options assumed were estimated using the following assumptions: Expected volatility 47 % Expected term (in years) 2.0 - 6.8 Risk-free interest rate 0.15% - 1.29% Dividend yield — %

Net Income (Loss) Per Share (Ta

Net Income (Loss) Per Share (Tables)	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Schedule of Earnings Per Share, Basic and Diluted	The numerators and denominators of the basic and diluted EPS computations for our common stock are calculated as follows (in millions, except for per share amounts): Year ended December 31, 2022 2021 Class A Class B Class A Class B Basic net income per share: Numerator Net income attributable to common stockholders $ 426.8 $ 126.4 $ 263.9 $ 71.9 Denominator Weighted-average number of common shares outstanding used in computing basic net income per share 278.6 82.6 304.9 83.1 Net income per common share, basic $ 1.53 $ 1.53 $ 0.87 $ 0.87 Diluted net income per share: Numerator Net income attributable to common stockholders $ 426.8 $ 126.4 $ 263.9 $ 71.9 Reallocation of net income as a result of conversion of Class B to Class A common stock $ 126.4 $ — $ 71.9 $ — Reallocation of net income to Class B common stock $ — $ (0.7) $ — $ (1.3) Net income attributable to common stockholders for diluted EPS $ 553.2 $ 125.7 $ 335.8 $ 70.6 Denominator Weighted-average number of common shares outstanding used in computing basic net income per share 278.6 82.6 304.9 83.1 Weighted-average effect of dilutive restricted stock units and awards and employee stock options 2.1 — 7.8 0.1 Conversion of Class B to Class A common stock 82.6 — 83.1 — Weighted-average number of common shares outstanding used in computing diluted net income per share 363.3 82.6 395.8 83.2 Net income per common share, diluted $ 1.52 $ 1.52 $ 0.85 $ 0.85 The following table sets forth the calculation of basic and diluted net loss per share attributable to common stockholders during the periods presented. The voluntary conversions of Class B common stock into Class A common stock are included in the table below weighted for the respective periods outstanding. Year ended December 31, 2020 Class A Class B Numerator: Net loss attributable to common stockholders $ (182.5) $ (73.8) Denominator: Weighted-average number of common shares outstanding used in computing basic and diluted net loss per common share 295.0 119.3 Net loss per common share, basic and diluted $ (0.62) $ (0.62)
Schedule of Potentially Dilutive Securities Excluded from Computation of Earnings Per Share	The weighted-average impact of potentially dilutive securities that were not included in the diluted per share calculations because they would be anti-dilutive was as follows: Year ended December 31, 2022 2021 2020 Restricted stock units and awards 20.4 2.4 10.5 Options to purchase shares of common stock 0.3 0.1 0.9 Co-Founder Grants 8.3 9.3 11.3 Convertible Senior Notes 37.8 31.9 — Warrants 37.8 31.9 — Total 104.6 75.6 22.7

Income Taxes (Tables)

Income Taxes (Tables)	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Schedule of Income before Income Tax, Domestic and Foreign	For the years ended December 31, 2022, 2021, and 2020, the Company’s income (loss) from continuing operations before provision for income taxes was as follows: Year ended December 31, 2022 2021 2020 Domestic $ 37.8 $ 185.3 $ (57.7) Foreign 154.9 114.0 (192.5) Income (loss) before income taxes $ 192.7 $ 299.3 $ (250.2)
Schedule of Components of Income Tax Expense (Benefit)	The components of the benefit from (provision for) income taxes in the years ended December 31, 2022, 2021, and 2020, were as follows: Year ended December 31, 2022 2021 2020 Current: Federal $ (13.2) $ (0.4) $ — State (15.3) (0.7) (2.7) Foreign (7.5) (2.5) (6.0) Deferred: Federal 386.7 2.2 — State 30.0 0.4 — Foreign (20.2) 37.5 2.6 Benefit from (provision for) income taxes $ 360.5 $ 36.5 $ (6.1)
Schedule of Effective Income Tax Rate Reconciliation	A reconciliation of income taxes at the statutory federal income tax rate to the benefit from (provision for) income taxes included in the accompanying consolidated statements of operations is as follows: Year ended December 31, 2022 2021 2020 Tax (provision) benefit at federal statutory rate $ (40.5) $ (62.8) $ 52.5 State taxes, net of federal benefit (4.9) (5.5) 1.2 Foreign rate differential (34.0) 0.9 (12.2) Research and other credits 45.3 38.1 34.9 Non-deductible compensation (3.4) (6.2) (4.1) Permanent differences (1.8) (0.8) (1.8) Change in valuation allowance 409.9 51.4 (69.6) Stock-based compensation (4.3) 23.5 (3.2) Other non-deductible items (5.8) (2.1) (3.8) Benefit from (provision for) income taxes $ 360.5 $ 36.5 $ (6.1)
Schedule of Deferred Tax Assets and Liabilities	The significant components of the Company’s deferred tax assets and liabilities as of December 31, 2022 and 2021 were as follows: As of December 31, 2022 2021 Deferred tax assets: Net operating loss carryforwards $ 40.8 $ 202.6 Research credit carryforwards 268.9 263.9 Stock-based compensation 24.1 25.2 Accruals and reserves 36.8 41.6 Lease liability 141.8 168.4 Convertible senior notes 47.5 57.3 Capitalized research expenditures 123.9 — Other 0.6 — Gross deferred tax assets 684.4 759.0 Valuation allowance (111.6) (586.7) Total deferred tax assets, net of valuation allowance 572.8 172.3 Deferred tax liabilities: Fixed assets and intangible assets 14.4 20.6 Right-of-use assets 59.5 110.2 Other 0.2 0.3 Total deferred tax liability 74.1 131.1 Net deferred tax assets $ 498.7 $ 41.2
Schedule of Unrecognized Tax Benefits Roll Forward	A reconciliation of the beginning and ending amount of unrecognized tax benefit is as follows: Year ended December 31, 2022 2021 2020 Balance of gross unrecognized tax benefits at the beginning of the fiscal year $ 107.3 $ 91.4 $ 74.5 Gross increases related to prior period tax positions — — 1.3 Gross decreases related to prior period tax positions — (0.3) — Gross increases related to current period tax positions 20.3 18.5 15.8 Reductions due to lapse in statute of limitations (0.4) (1.5) (0.2) Reductions due to settlements with taxing authorities — (0.8) — Balance of gross unrecognized tax benefits at the end of the fiscal year $ 127.2 $ 107.3 $ 91.4

Geographic Areas (Tables)

Geographic Areas (Tables)	12 Months Ended
	Dec. 31, 2022
Segment Reporting [Abstract]
Long-lived Assets by Geographic Areas	The following table sets forth long-lived assets by geographic area: As of December 31, 2022 2021 United States $ 300.2 $ 316.6 International (1) 8.2 5.4 Total property and equipment, net $ 308.4 $ 322.0 (1) No single country other than the United States had a property and equipment balance greater than 10% of total property and equipment, net, as of December 31, 2022 and 2021.
Revenue by Geographic Areas	The following table sets forth revenue by geographic area for the years ended December 31, 2022, 2021, and 2020: Year ended December 31, 2022 2021 2020 United States $ 1,264.2 $ 1,130.0 $ 999.3 International (1) 1,060.7 1,027.9 914.6 Total revenue $ 2,324.9 $ 2,157.9 $ 1,913.9

Description of the Business a_4

Description of the Business and Summary of Significant Accounting Policies - Foreign Currency Transactions (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Net foreign currency transaction gains (losses)	$ 0.2	$ (1.8)

Description of the Business a_5

Description of the Business and Summary of Significant Accounting Policies - Revenue Recognition (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Revenue, performance obligation, description of timing	one year or longer
Revenue recognized	$ 671.5	$ 610.5	$ 554.2
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2023-01-01
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Remaining performance obligation	$ 774.2
Remaining performance obligation, expected timing of satisfaction	12 months

Description of the Business a_6

Description of the Business and Summary of Significant Accounting Policies - Stock-based Compensation (Details) - Restricted Stock - shares shares in Millions	1 Months Ended	12 Months Ended
	Dec. 31, 2017	Dec. 31, 2022	Dec. 31, 2021
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting period		4 years
Shares granted (in shares)		27.8	19.6
Chief Executive Officer | Co-Founder Grants
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares granted (in shares)	10.3

Description of the Business a_7

Description of the Business and Summary of Significant Accounting Policies - Advertising and promotional expense (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Advertising and promotional expense	$ 94.8	$ 108.6	$ 81.4

Description of the Business a_8

Description of the Business and Summary of Significant Accounting Policies - Concentrations of Credit Risk (Details) - Customer Concentration Risk - Trade and Other Receivables	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Customer A
Concentration Risk [Line Items]
Concentration risk, percentage	12%	14%
Customer B
Concentration Risk [Line Items]
Concentration risk, percentage	30%	29%

Description of the Business a_9

Description of the Business and Summary of Significant Accounting Policies - Receivables (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Allowance for doubtful accounts	$ 0.7	$ 1
Non-trade receivables	$ 6.5	$ 4.1

Description of the Business _10

Description of the Business and Summary of Significant Accounting Policies - Deferred Commissions, Net (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Capitalized Contract Cost [Line Items]
Additional contract costs deferred	$ 33.5	$ 23.7
Deferred contract costs, amortization period	5 years
Amortization of deferred commissions	$ 39.5	32.3	$ 24.4
Renewal Commissions
Capitalized Contract Cost [Line Items]
Deferred contract costs, amortization period	1 year
Prepaid Expenses and Other Current Assets | Deferred Commissions
Capitalized Contract Cost [Line Items]
Deferred contract costs	$ 33.6	30.8
Other Assets | Deferred Commissions
Capitalized Contract Cost [Line Items]
Deferred contract costs	$ 25.7	$ 34.6

Description of the Business _11

Description of the Business and Summary of Significant Accounting Policies - Property and Equipment, Net (Details)	12 Months Ended
	Dec. 31, 2022
Minimum
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	3 years
Minimum | Buildings
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	20 years
Minimum | Datacenter and other computer equipment
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	3 years
Minimum | Office equipment and other
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	3 years
Maximum
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	7 years
Maximum | Buildings
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	30 years
Maximum | Datacenter and other computer equipment
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	5 years
Maximum | Office equipment and other
Property, Plant and Equipment [Line Items]
Property and equipment, useful life	7 years

Description of the Business _12

Description of the Business and Summary of Significant Accounting Policies - Lease obligations (Details) - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Impairment related to real estate assets	[1],[2]	$ 175.2	$ 31.3	$ 398.2
[1]Includes impairment charges related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted the Company's subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information.[2]Includes stock-based compensation as follows (in millions): Year ended December 31, 2022 2021 2020 Cost of revenue $ 24.7 $ 23.2 $ 17.1 Research and development 232.3 190.1 174.1 Sales and marketing 22.4 25.0 33.7 General and administrative (4) 51.3 48.8 36.6

Description of the Business _13

Description of the Business and Summary of Significant Accounting Policies - Long-lived assets, including goodwill and other acquired intangible assets, net (Details) - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Goodwill		$ 403.3	$ 356.6
Impairment related to real estate assets	[1],[2]	$ 175.2	$ 31.3	$ 398.2
[1]Includes impairment charges related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted the Company's subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information.[2]Includes stock-based compensation as follows (in millions): Year ended December 31, 2022 2021 2020 Cost of revenue $ 24.7 $ 23.2 $ 17.1 Research and development 232.3 190.1 174.1 Sales and marketing 22.4 25.0 33.7 General and administrative (4) 51.3 48.8 36.6

Description of the Business _14

Description of the Business and Summary of Significant Accounting Policies - Income taxes (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Income tax benefit, release of deferred tax asset valuation allowance	$ 420.2	$ 38.1

Cash, Cash Equivalents and Sh_3

Cash, Cash Equivalents and Short-Term Investments - Schedule of Cash, Cash Equivalents and Short-Term Investments (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Cash and Cash Equivalents [Line Items]
Cash and cash equivalents, amortized cost	$ 232.8	$ 533
Cash and cash equivalents, estimated fair value	232.8	533
Short-term investments, amortized cost	1,158.5	1,193.8
Short-term investments, unrealized gain	0.3	0.5
Short-term investments, unrealized loss	(48.2)	(9.2)
Short-term investments, estimated fair value	1,110.6	1,185.1
Total cash, cash equivalents, and short term investments, before unrealized gain (loss) on investments	1,391.3	1,726.8
Total cash, cash equivalents, and short term investments	1,343.4	1,718.1
Corporate notes and obligations
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	512.1	607.4
Short-term investments, unrealized gain	0.1	0.4
Short-term investments, unrealized loss	(22.7)	(4)
Short-term investments, estimated fair value	489.5	603.8
U.S. Treasury securities
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	360.2	240.4
Short-term investments, unrealized gain	0.2	0
Short-term investments, unrealized loss	(14)	(2.9)
Short-term investments, estimated fair value	346.4	237.5
Asset backed securities
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	117.6	140.7
Short-term investments, unrealized gain	0	0.1
Short-term investments, unrealized loss	(6)	(1.2)
Short-term investments, estimated fair value	111.6	139.6
Municipal securities
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	65.3	70.5
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	(4.1)	(0.7)
Short-term investments, estimated fair value	61.2	69.8
Commercial paper
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	46.4	61.7
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	0	0
Short-term investments, estimated fair value	46.4	61.7
Certificates of deposit
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	29.1	32.1
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	0	0
Short-term investments, estimated fair value	29.1	32.1
U.S. agency obligations
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	18.4	14.6
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	(0.8)	(0.2)
Short-term investments, estimated fair value	17.6	14.4
Foreign government obligations
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	6	18.4
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	(0.4)	(0.1)
Short-term investments, estimated fair value	5.6	18.3
Supranational securities
Cash and Cash Equivalents [Line Items]
Short-term investments, amortized cost	3.4	8
Short-term investments, unrealized gain	0	0
Short-term investments, unrealized loss	(0.2)	(0.1)
Short-term investments, estimated fair value	3.2	7.9
Cash
Cash and Cash Equivalents [Line Items]
Cash and cash equivalents, amortized cost	90.1	142.7
Cash and cash equivalents, estimated fair value	90.1	142.7
Money market funds
Cash and Cash Equivalents [Line Items]
Cash and cash equivalents, amortized cost	139.5	390.3
Cash and cash equivalents, estimated fair value	139.5	$ 390.3
Commercial paper
Cash and Cash Equivalents [Line Items]
Cash and cash equivalents, amortized cost	3.2
Cash and cash equivalents, estimated fair value	$ 3.2

Cash, Cash Equivalents and Sh_4

Cash, Cash Equivalents and Short-Term Investments - Narrative (Details) $ in Millions	12 Months Ended
	Dec. 31, 2022 USD ($) investment_type investment	Dec. 31, 2021 USD ($)	Dec. 31, 2020 USD ($)
Cash and Cash Equivalents [Abstract]
Cash in transit for credit and debit card transactions	$ 12.4	$ 8.3
Number of investments in unrealized loss positions | investment	710
Number of security types | investment_type	9
Number of security types in loss position | investment_type	7
Unrealized losses, short term investments	$ 48.2	9.2
Investment income	$ 15.7	$ 7.5	$ 12.5

Cash, Cash Equivalents and Sh_5

Cash, Cash Equivalents and Short-Term Investments - Contractual Maturities of Short Term Investments (Details) $ in Millions	Dec. 31, 2022 USD ($)
Amortized cost
Due within one year	$ 398.6
Due between one to three years	556.8
Due after three years	203.1
Total	1,158.5
Estimated fair value
Due within one year	393.5
Due between one to three years	531.8
Due after three years	185.3
Total	$ 1,110.6

Cash, Cash Equivalents and Sh_6

Cash, Cash Equivalents and Short-Term Investments - Unrealized Loss Position Aggregated By Investment (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Less than 12 months
Fair Value	$ 314.3	$ 941
Gross Unrealized Losses	(6)	(9.2)
More than 12 months
Fair Value	633.7	0
Gross Unrealized Losses	(42.2)	0
Total
Fair Value	948	941
Gross Unrealized Losses	(48.2)	(9.2)
Corporate notes and obligations
Less than 12 months
Fair Value	176.5	498.6
Gross Unrealized Losses	(3.5)	(4)
More than 12 months
Fair Value	292.3	0
Gross Unrealized Losses	(19.2)	0
Total
Fair Value	468.8	498.6
Gross Unrealized Losses	(22.7)	(4)
U.S. Treasury securities
Less than 12 months
Fair Value	110.9	218
Gross Unrealized Losses	(1.8)	(2.9)
More than 12 months
Fair Value	176.9	0
Gross Unrealized Losses	(12.2)	0
Total
Fair Value	287.8	218
Gross Unrealized Losses	(14)	(2.9)
Asset backed securities
Less than 12 months
Fair Value	13.7	120.7
Gross Unrealized Losses	(0.4)	(1.2)
More than 12 months
Fair Value	90.4	0
Gross Unrealized Losses	(5.6)	0
Total
Fair Value	104.1	120.7
Gross Unrealized Losses	(6)	(1.2)
Municipal securities
Less than 12 months
Fair Value	9.3	66
Gross Unrealized Losses	(0.3)	(0.7)
More than 12 months
Fair Value	51.6	0
Gross Unrealized Losses	(3.8)	0
Total
Fair Value	60.9	66
Gross Unrealized Losses	(4.1)	(0.7)
U.S. agency obligations
Less than 12 months
Fair Value	3.9	14.4
Gross Unrealized Losses	0	(0.2)
More than 12 months
Fair Value	13.8	0
Gross Unrealized Losses	(0.8)	0
Total
Fair Value	17.7	14.4
Gross Unrealized Losses	(0.8)	(0.2)
Foreign government obligations
Less than 12 months
Fair Value	0	15.4
Gross Unrealized Losses	0	(0.1)
More than 12 months
Fair Value	5.5	0
Gross Unrealized Losses	(0.4)	0
Total
Fair Value	5.5	15.4
Gross Unrealized Losses	(0.4)	(0.1)
Supranational securities
Less than 12 months
Fair Value	0	7.9
Gross Unrealized Losses	0	(0.1)
More than 12 months
Fair Value	3.2	0
Gross Unrealized Losses	(0.2)	0
Total
Fair Value	3.2	7.9
Gross Unrealized Losses	$ (0.2)	$ (0.1)

Fair Value Measurements - Fair

Fair Value Measurements - Fair Value on Recurring Basis (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	$ 232.8	$ 533
Short-term investments	1,110.6	1,185.1
Corporate notes and obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	489.5	603.8
U.S. Treasury securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	346.4	237.5
Asset backed securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	111.6	139.6
Municipal securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	61.2	69.8
Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	46.4	61.7
Certificates of deposit
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	29.1	32.1
Foreign government obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	5.6	18.3
U.S. agency obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	17.6	14.4
Supranational securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	3.2	7.9
Money market funds
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	139.5	390.3
Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	3.2
Fair Value, Measurements, Recurring
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	142.7	390.3
Short-term investments	1,110.6	1,185.1
Assets, fair value disclosure	1,253.3	1,575.4
Fair Value, Measurements, Recurring | Corporate notes and obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	489.5	603.8
Fair Value, Measurements, Recurring | U.S. Treasury securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	346.4	237.5
Fair Value, Measurements, Recurring | Asset backed securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	111.6	139.6
Fair Value, Measurements, Recurring | Municipal securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	61.2	69.8
Fair Value, Measurements, Recurring | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	46.4	61.7
Fair Value, Measurements, Recurring | Certificates of deposit
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	29.1	32.1
Fair Value, Measurements, Recurring | Foreign government obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	5.6	18.3
Fair Value, Measurements, Recurring | U.S. agency obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	17.6	14.4
Fair Value, Measurements, Recurring | Supranational securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	3.2	7.9
Fair Value, Measurements, Recurring | Money market funds
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	139.5	390.3
Fair Value, Measurements, Recurring | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	3.2
Fair Value, Measurements, Recurring | Level 1
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	139.5	390.3
Short-term investments	0	0
Assets, fair value disclosure	139.5	390.3
Fair Value, Measurements, Recurring | Level 1 | Corporate notes and obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | U.S. Treasury securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Asset backed securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Municipal securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Certificates of deposit
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Foreign government obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | U.S. agency obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Supranational securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 1 | Money market funds
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	139.5	390.3
Fair Value, Measurements, Recurring | Level 1 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	0
Fair Value, Measurements, Recurring | Level 2
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	3.2	0
Short-term investments	1,110.6	1,185.1
Assets, fair value disclosure	1,113.8	1,185.1
Fair Value, Measurements, Recurring | Level 2 | Corporate notes and obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	489.5	603.8
Fair Value, Measurements, Recurring | Level 2 | U.S. Treasury securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	346.4	237.5
Fair Value, Measurements, Recurring | Level 2 | Asset backed securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	111.6	139.6
Fair Value, Measurements, Recurring | Level 2 | Municipal securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	61.2	69.8
Fair Value, Measurements, Recurring | Level 2 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	46.4	61.7
Fair Value, Measurements, Recurring | Level 2 | Certificates of deposit
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	29.1	32.1
Fair Value, Measurements, Recurring | Level 2 | Foreign government obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	5.6	18.3
Fair Value, Measurements, Recurring | Level 2 | U.S. agency obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	17.6	14.4
Fair Value, Measurements, Recurring | Level 2 | Supranational securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	3.2	7.9
Fair Value, Measurements, Recurring | Level 2 | Money market funds
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	0	0
Fair Value, Measurements, Recurring | Level 2 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	3.2
Fair Value, Measurements, Recurring | Level 3
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	0	0
Short-term investments	0	0
Assets, fair value disclosure	0	0
Fair Value, Measurements, Recurring | Level 3 | Corporate notes and obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | U.S. Treasury securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Asset backed securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Municipal securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Certificates of deposit
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Foreign government obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | U.S. agency obligations
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Supranational securities
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Short-term investments	0	0
Fair Value, Measurements, Recurring | Level 3 | Money market funds
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	0	$ 0
Fair Value, Measurements, Recurring | Level 3 | Commercial paper
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Cash equivalents	$ 0

Fair Value Measurements - Narra

Fair Value Measurements - Narrative (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Equity securities, FV-NI, realized gain	$ 5
Level 3
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Equity securities, FV-NI		$ 5.6
2026 Notes
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Convertible debt, fair value disclosures	631.5
2026 Notes | Convertible Debt
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Debt instrument, face amount	$ 695.8
Debt instrument, interest rate, stated percentage	0%
2028 Notes
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Convertible debt, fair value disclosures	$ 632.2
2028 Notes | Convertible Debt
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Debt instrument, face amount	$ 693.3
Debt instrument, interest rate, stated percentage	0%

Property and Equipment, Net - S

Property and Equipment, Net - Schedule of Property and Equipment, Net (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Property, Plant and Equipment [Line Items]
Total property and equipment	$ 811.9	$ 774.6
Accumulated depreciation and amortization	(503.5)	(452.6)
Property and equipment, net	308.4	322
Datacenter and other computer equipment
Property, Plant and Equipment [Line Items]
Total property and equipment	671.3	634.5
Furniture and fixtures
Property, Plant and Equipment [Line Items]
Total property and equipment	19.8	21.7
Leasehold improvements
Property, Plant and Equipment [Line Items]
Total property and equipment	118	106.7
Construction in progress
Property, Plant and Equipment [Line Items]
Total property and equipment	$ 2.8	$ 11.7

Property and Equipment, Net - N

Property and Equipment, Net - Narrative (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Property, Plant and Equipment [Abstract]
Assets under equipment finance lease, gross	$ 456.4	$ 469.4
Assets under equipment finance lease, accumulated depreciation	240.9	237.6
Depreciation	$ 140.9	$ 135.7

Business Combinations - Narrati

Business Combinations - Narrative (Details) - USD ($) $ in Millions			12 Months Ended
	Dec. 15, 2022	Mar. 22, 2021	Dec. 31, 2022	Dec. 31, 2021
FormSwift
Business Acquisition [Line Items]
Percentage of business acquired	100%
Purchase consideration, agreements with key personnel	$ 25.7
Required service period	3 years
Acquired finite-lived intangible assets weighted average amortization period	3 years 8 months 12 days
Acquisition-related diligence costs			$ 1.3
DocSend Inc.
Business Acquisition [Line Items]
Purchase consideration, agreements with key personnel		$ 30.7	20.5
Required service period		3 years
Acquired finite-lived intangible assets weighted average amortization period		5 years
Acquisition-related diligence costs				$ 1.2
Personnel agreement, expense recognized			$ 10.2

Business Combinations - Schedul

Business Combinations - Schedule of Purchase Consideration (Details) - USD ($) $ in Millions	Dec. 15, 2022	Mar. 22, 2021
FormSwift
Business Acquisition [Line Items]
Cash paid to common and preferred stockholders and vested option holders	$ 50
Cash paid for extinguishing shadow stock units	3.2
Transaction costs paid by Dropbox on behalf of DocSend	2
Cash purchase consideration	55.2
Indemnification holdback	14.3
Total purchase consideration	$ 69.5
Indemnity holdback period	18 months
DocSend Inc.
Business Acquisition [Line Items]
Cash paid to common and preferred stockholders and vested option holders		$ 125.5
Transaction costs paid by Dropbox on behalf of DocSend		5
Fair value of assumed options attributable to pre-combination services		1.2
Cash purchase consideration		0.1
Total purchase consideration		$ 131.8

Business Combinations - Sched_2

Business Combinations - Schedule of Recognized Identified Assets Acquired and Liabilities Assumed (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 15, 2022	Dec. 31, 2021	Mar. 22, 2021
Liabilities assumed:
Goodwill	$ 403.3		$ 356.6
FormSwift
Assets acquired:
Cash and cash equivalents		$ 0.4
Acquisition-related intangible assets		41.2
Accounts receivable, prepaid and other assets		3.4
Total assets acquired		45
Liabilities assumed:
Accounts payable, accrued and other liabilities		4.6
Deferred revenue		6.6
Total liabilities assumed		11.2
Net assets acquired, excluding goodwill		33.8
Total purchase consideration		69.5
Goodwill		$ 35.7
DocSend Inc.
Assets acquired:
Cash and cash equivalents				$ 5.1
Acquisition-related intangible assets				20.6
Accounts receivable, prepaid and other assets				6.1
Total assets acquired				31.8
Liabilities assumed:
Accounts payable, accrued and other liabilities				6.4
Deferred revenue				1.9
Deferred tax liability				1.9
Total liabilities assumed				10.2
Net assets acquired, excluding goodwill				21.6
Total purchase consideration				131.8
Goodwill				$ 110.2

Business Combinations - Sched_3

Business Combinations - Schedule of Assets Acquired (Details) - USD ($) $ in Millions	Dec. 15, 2022	Mar. 22, 2021
DocSend Inc.
Business Acquisition [Line Items]
Estimated fair values		$ 20.6
Estimated weighted average useful lives (In years)		5 years
FormSwift
Business Acquisition [Line Items]
Estimated fair values	$ 41.2
Estimated weighted average useful lives (In years)	3 years 8 months 12 days
Developed technology | DocSend Inc.
Business Acquisition [Line Items]
Estimated fair values		$ 11.5
Estimated weighted average useful lives (In years)		5 years
Developed technology | FormSwift
Business Acquisition [Line Items]
Estimated fair values	$ 24.2
Estimated weighted average useful lives (In years)	5 years
Customer relationships | DocSend Inc.
Business Acquisition [Line Items]
Estimated fair values		$ 8.1
Estimated weighted average useful lives (In years)		5 years
Customer relationships | FormSwift
Business Acquisition [Line Items]
Estimated fair values	$ 16.4
Estimated weighted average useful lives (In years)	2 years
Trade name | DocSend Inc.
Business Acquisition [Line Items]
Estimated fair values		$ 1
Estimated weighted average useful lives (In years)		5 years
Trade name | FormSwift
Business Acquisition [Line Items]
Estimated fair values	$ 0.6
Estimated weighted average useful lives (In years)	1 year

Intangible Assets - Schedule of

Intangible Assets - Schedule of Intangible Assets (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 160.7	$ 117
Accumulated amortization	(72.4)	(63.4)
Intangible assets, net	88.3	53.6
Developed technology
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 74.3	45.9
Developed technology | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	4 years 2 months 12 days
Customer relationships
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 43.2	28.6
Customer relationships | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	2 years 2 months 12 days
Patents
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 19.4	19.5
Patents | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	4 years 3 months 18 days
Software
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 8.9	9
Software | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	8 months 12 days
Trademarks and trade names
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 5.8	5.6
Trademarks and trade names | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	1 year 7 months 6 days
Licenses
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 4.6	4.6
Licenses | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	0 years
Assembled workforce in asset acquisitions
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 3.4	3
Assembled workforce in asset acquisitions | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	3 years 3 months 18 days
Other
Finite-Lived Intangible Assets [Line Items]
Intangible assets, gross	$ 1.1	$ 0.8
Other | Weighted Average
Finite-Lived Intangible Assets [Line Items]
Weighted- average remaining useful life (In years)	2 years 9 months 18 days

Intangible Assets - Schedule _2

Intangible Assets - Schedule of Future Amortization Expense (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense	$ 16.3	$ 15.6	$ 14.1
Finite-Lived Intangible Assets, Amortization Expense, Maturity Schedule [Abstract]
2023	30.4
2024	25.1
2025	14.8
2026	10.4
2027	7
Thereafter	0.6
Total	$ 88.3

Goodwill (Details)

Goodwill (Details) - USD ($)	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Goodwill [Roll Forward]
Goodwill, beginning balance	$ 356,600,000
Effect of foreign currency translation	(3,400,000)
Goodwill, ending balance	403,300,000	$ 356,600,000
Goodwill impairment	0	$ 0	$ 0
FormSwift acquisition
Goodwill [Roll Forward]
Acquisitions	35,700,000
Other acquisition
Goodwill [Roll Forward]
Acquisitions	$ 14,400,000

Debt - Revolving Credit Facilit

Debt - Revolving Credit Facility (Details) - Credit and Guarantee Agreement - USD ($)	1 Months Ended
	Feb. 28, 2021	Feb. 28, 2018	Dec. 31, 2022	Apr. 30, 2017
Line of Credit
Line of Credit Facility [Line Items]
Covenant terms, minimum liquidity balance		$ 100,000,000
Revolving Credit Facility
Line of Credit Facility [Line Items]
Unused capacity, commitment fee percentage		0.20%
Revolving Credit Facility | Line of Credit
Line of Credit Facility [Line Items]
Line of credit facility, maximum borrowing capacity	$ 500,000,000	$ 725,000,000		$ 600,000,000
Line of credit facility, accordion feature, increase limit	250,000,000
Debt issuance fees	1,700,000
Write off of deferred debt issuance cost	$ 200,000
Aggregate letters of credit outstanding amount			$ 40,600,000
Remaining borrowing capacity			$ 459,400,000
Revolving Credit Facility | Line of Credit | LIBOR
Line of Credit Facility [Line Items]
Basis spread on variable rate		1.375%
Revolving Credit Facility | Line of Credit | Base Rate
Line of Credit Facility [Line Items]
Basis spread on variable rate		0.375%
Letter of Credit
Line of Credit Facility [Line Items]
Commitment fee percentage		1.375%
Fronting fee		0.125%
Letter of Credit | Line of Credit
Line of Credit Facility [Line Items]
Line of credit facility, maximum borrowing capacity		$ 187,500,000

Debt - Convertible Senior Notes

Debt - Convertible Senior Notes (Details) $ / shares in Units, $ in Millions	3 Months Ended	12 Months Ended
	Mar. 31, 2021 USD ($)	Dec. 31, 2022 USD ($) d $ / shares	Dec. 31, 2021 USD ($)	Dec. 31, 2020 USD ($)
Line of Credit Facility [Line Items]
Proceeds from issuance of convertible senior notes	$ 1,400	$ 0	$ 1,389.1	$ 0
2026 Notes
Line of Credit Facility [Line Items]
Debt instrument, convertible, conversion ratio		0.0261458
Convertible debt, conversion rate (in dollars per share) | $ / shares		$ 38.25
Interest expense		$ 2.1	1.9
2026 Notes | Maximum
Line of Credit Facility [Line Items]
Debt instrument, convertible, conversion ratio		0.0431406
2028 Notes
Line of Credit Facility [Line Items]
Debt instrument, convertible, conversion ratio		0.0282889
Convertible debt, conversion rate (in dollars per share) | $ / shares		$ 35.35
Interest expense		$ 1.6	$ 1.3
2028 Notes | Maximum
Line of Credit Facility [Line Items]
Debt instrument, convertible, conversion ratio		0.0431406
Convertible Debt | 2026 Notes
Line of Credit Facility [Line Items]
Proceeds from issuance of convertible senior notes	695.8
Debt issuance costs		$ 11
Debt instrument, term		5 years
Effective interest rate		0.32%
Convertible Debt | 2028 Notes
Line of Credit Facility [Line Items]
Proceeds from issuance of convertible senior notes	$ 693.3
Debt issuance costs		$ 11
Debt instrument, term		7 years
Effective interest rate		0.22%
Debt Conversion, Scenario One
Line of Credit Facility [Line Items]
Convertible debt, threshold trading days | d		20
Convertible debt, threshold consecutive trading days | d		30
Convertible debt, threshold percentage of stock price trigger		130%
Debt Conversion, Scenario Two
Line of Credit Facility [Line Items]
Convertible debt, threshold trading days | d		5
Convertible debt, threshold consecutive trading days | d		5
Convertible debt, threshold percentage of stock price trigger		98%
Debt Conversion, Scenario Three
Line of Credit Facility [Line Items]
Convertible debt, threshold trading days | d		20
Convertible debt, threshold consecutive trading days | d		30
Convertible debt, threshold percentage of stock price trigger		130%
Debt Conversion, Scenario Three | Convertible Debt
Line of Credit Facility [Line Items]
Convertible debt, redemption percentage		100%
Debt Conversion, Scenario Four | Convertible Debt
Line of Credit Facility [Line Items]
Convertible debt, redemption percentage		100%

Debt - Schedule of Convertible

Debt - Schedule of Convertible Notes (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Line of Credit Facility [Line Items]
Principal balance	$ 1,389.1
Convertible Debt
Line of Credit Facility [Line Items]
Principal balance	1,389.1	$ 1,389.1
Unamortized issuance costs	(15.1)	(18.8)
Carrying value, net	1,374	1,370.3
2026 Notes | Convertible Debt
Line of Credit Facility [Line Items]
Principal balance	695.8	695.8
Unamortized issuance costs	(7)	(9.1)
Carrying value, net	688.8	686.7
2028 Notes | Convertible Debt
Line of Credit Facility [Line Items]
Principal balance	693.3	693.3
Unamortized issuance costs	(8.1)	(9.7)
Carrying value, net	$ 685.2	$ 683.6

Debt - Long Term Debt Maturitie

Debt - Long Term Debt Maturities (Details) $ in Millions	Dec. 31, 2022 USD ($)
Debt Disclosure [Abstract]
2023	$ 0
2024	0
2025	0
2026	695.8
2027	0
Thereafter	693.3
Total	$ 1,389.1

Debt - Convertible Note Hedges

Debt - Convertible Note Hedges and Warrants (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Line of Credit Facility [Line Items]
Proceeds from sale of warrants in connection with issuance of convertible senior notes	$ 0	$ 202.9	$ 0
2026 Notes
Line of Credit Facility [Line Items]
Convertible debt, conversion rate (in dollars per share)	$ 38.25
Convertible debt, effective conversion rate (in dollars per share)	46.36
2028 Notes
Line of Credit Facility [Line Items]
Convertible debt, conversion rate (in dollars per share)	35.35
Convertible debt, effective conversion rate (in dollars per share)	$ 46.36
2026 and 2028 Warrants
Line of Credit Facility [Line Items]
Proceeds from sale of warrants in connection with issuance of convertible senior notes	$ 202.9
2026 Warrants
Line of Credit Facility [Line Items]
Number of shares covered by warrant (in shares)	18.1
Warrant price (in dollars per share)	$ 46.36
2028 Warrants
Line of Credit Facility [Line Items]
Number of shares covered by warrant (in shares)	20.1
Warrant price (in dollars per share)	$ 46.36
2026 Notes Hedge
Line of Credit Facility [Line Items]
Convertible note hedge, number of shares covered by hedge (in shares)	18.2
Convertible note hedge, strike price (in dollars per share)	$ 38.25
2028 Notes Hedge
Line of Credit Facility [Line Items]
Convertible note hedge, number of shares covered by hedge (in shares)	19.6
Convertible note hedge, strike price (in dollars per share)	$ 35.35
Convertible Note Hedge
Line of Credit Facility [Line Items]
Cost of note hedge transaction	$ 265.3

Leases - Narrative (Details)

Leases - Narrative (Details) - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2017
Lessee, Lease, Description [Line Items]
Lease, renewal term		5 years
Operating sublease, extension term		4 years
Sublease income		$ 20.1	$ 17.6
Impairment related to real estate assets	[1],[2]	175.2	$ 31.3	$ 398.2
Operating leases, not yet commenced, value		$ 1
Operating leases, not yet commenced, term of contract		2 years
Minimum
Lessee, Lease, Description [Line Items]
Lease, remaining lease term		1 year
Operating sublease, term		1 year
Maximum
Lessee, Lease, Description [Line Items]
Lease, remaining lease term		14 years
Operating sublease, term		10 years
Corporate Headquarters Lease
Lessee, Lease, Description [Line Items]
Operating lease, term of contract					15 years
Minimum obligations		$ 553.2
Corporate Headquarters Lease | Line of Credit | Letter of Credit
Lessee, Lease, Description [Line Items]
Letter of credit		$ 26.1
[1]Includes impairment charges related to real estate assets as a result of adverse changes in the corporate real estate market which has impacted the Company's subleasing strategy in conjunction with its shift to Virtual First. See Note 9 "Leases" for further information.[2]Includes stock-based compensation as follows (in millions): Year ended December 31, 2022 2021 2020 Cost of revenue $ 24.7 $ 23.2 $ 17.1 Research and development 232.3 190.1 174.1 Sales and marketing 22.4 25.0 33.7 General and administrative (4) 51.3 48.8 36.6

Leases - Components of Lease Ex

Leases - Components of Lease Expense (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Leases [Abstract]
Operating lease, cost	$ 91.7	$ 107.8
Finance lease cost:
Amortization of assets under finance lease	111.4	107.1
Interest	7.5	8.8
Total finance lease cost	$ 118.9	$ 115.9

Leases - Other Lease Informatio

Leases - Other Lease Information (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Leases [Abstract]
Payments for operating leases included in cash from operating activities	$ 104.7	$ 130.3
Payments for finance leases included in cash from operating activities	7.5	8.8
Payments for finance leases included in cash from financing activities	127.5	110.4	$ 89.5
Operating leases	33	67.1
Finance leases	$ 105.8	$ 127.3
Weighted average remaining lease term (in years) - operating leases	9 years 10 months 24 days	10 years 2 months 12 days
Weighted average remaining lease term (in years) - finance leases	2 years 7 months 6 days	2 years 8 months 12 days
Weighted average discount rate - operating leases	4.10%	4%
Weighted average discount rate - finance leases	3.40%	2.90%

Leases - Schedule of Future Min

Leases - Schedule of Future Minimum Payments (Details) $ in Millions	Dec. 31, 2022 USD ($)
Operating leases
2023	$ 94.7
2024	89.9
2025	84.5
2026	64.9
2027	65.1
Thereafter	411.7
Total future minimum lease payments	810.8
Less imputed interest	(155.5)
Less tenant improvement receivables	(1.2)
Total liability	654.1
Finance leases
2023	121.9
2024	87.4
2025	49.4
2026	21.1
2027	0.2
Thereafter	0
Total future minimum lease payments	280
Less imputed interest	(13.5)
Less tenant improvement receivables	0
Total liability	$ 266.5

Leases - Future Subtenant Payme

Leases - Future Subtenant Payments Receivable (Details) $ in Millions	Dec. 31, 2022 USD ($)
Leases [Abstract]
2023	$ 17.5
2024	16.7
2025	15.6
2026	11.9
2027	8.2
Thereafter	26.4
Total future sublease rent payments	96.3
Less subtenant incentive	(1.1)
Total future sublease rent payments, net	$ 95.2

Commitments and Contingencies -

Commitments and Contingencies - Future Minimum Payments (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Finance lease commitments
2023	$ 121.9
2024	87.4
2025	49.4
2026	21.1
2027	0.2
Thereafter	0
Total future minimum lease payments	280
Less interest and taxes	(13.5)
Less current portion of the present value of minimum lease payments	(114.8)	$ (120.4)
Finance lease liability, non-current	151.7	$ 167.7
Operating lease commitments
2023	94.7
2024	89.9
2025	84.5
2026	64.9
2027	65.1
Thereafter	411.7
Future minimum payments	810.8
Other Commitments
2023	43.6
2024	4.1
2025	1.1
2026	0.4
2027	0
Thereafter	17.6
Future minimum payments	$ 66.8

Accrued and Other Current Lia_3

Accrued and Other Current Liabilities (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Payables and Accruals [Abstract]
Non-income taxes payable	$ 76.4	$ 77.4
Accrued legal and other external fees	25.5	24
Other accrued and current liabilities	38	39.4
Total accrued and other current liabilities	$ 139.9	$ 140.8

Stockholders_ (Deficit) Equit_2

Stockholders’ (Deficit) Equity - Common and Preferred Stock (Details)	1 Months Ended	12 Months Ended
	Dec. 31, 2017 shares	Dec. 31, 2022 investment $ / shares shares	Dec. 31, 2021 $ / shares shares
Class of Stock [Line Items]
Common stock, par value (in dollars per share) | $ / shares		$ 0.00001	$ 0.00001
Common stock, shares issued (in shares)			292,700,000
Preferred stock, shares authorized (in shares)		240,000,000	240,000,000
Restricted Stock
Class of Stock [Line Items]
Shares granted (in shares)		27,800,000	19,600,000
Co-Founder Grants | Restricted Stock | Chief Executive Officer
Class of Stock [Line Items]
Shares granted (in shares)	10,300,000
Class A Common Stock
Class of Stock [Line Items]
Votes per share | investment		1
Common stock, shares authorized (in shares)		2,400,000,000	2,400,000,000
Common stock, par value (in dollars per share) | $ / shares		$ 0.00001
Common stock, shares issued (in shares)		267,200,000	292,700,000
Common stock, shares outstanding (in shares)		267,200,000	292,700,000
Shares granted (in shares)		8,300,000	8,300,000
Class B Common Stock
Class of Stock [Line Items]
Votes per share | investment		10
Common stock, shares authorized (in shares)		475,000,000	475,000,000
Common stock, par value (in dollars per share) | $ / shares		$ 0.00001
Shares converted in conversion (in shares)		600,000	700,000
Common stock, shares issued (in shares)		82,200,000	82,800,000
Common stock, shares outstanding (in shares)		82,200,000	82,800,000
Class C Common Stock
Class of Stock [Line Items]
Votes per share | investment		0
Common stock, shares authorized (in shares)		800,000,000	800,000,000
Common stock, par value (in dollars per share) | $ / shares		$ 0.00001
Common stock, shares issued (in shares)		0	0
Common stock, shares outstanding (in shares)		0	0

Stockholders_ (Deficit) Equit_3

Stockholders’ (Deficit) Equity - Stock Repurchase Program (Details) - USD ($) shares in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Feb. 28, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock repurchase program, authorized amount			$ 1,200,000,000
Class A
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock repurchased and retired during period (in shares)	35.6	41.1
Stock repurchased and retired during period, aggregate purchase price	$ 795,400,000	$ 1,100,000,000
Convertible Debt | Class A
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock repurchased and retired during period (in shares)	8.6
Stock repurchased and retired during period, aggregate purchase price	$ 200,000,000

Stockholders_ (Deficit) Equit_4

Stockholders’ (Deficit) Equity - Equity Incentive Plans (Details) - USD ($) shares in Millions, $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares issued and outstanding (in shares)	0.4	0.9	1.3
2018 Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period	10 years
Remaining unamortized stock-based compensation	$ 772.2
Award requisite period	2 years 9 months 18 days
2018 Plan | Employee Stock Option
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period	10 years
Vesting period	4 years
Dropbox, Dropbox Sign And Doc Send Equity Incentive Plans
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares issued and outstanding (in shares)	34.8
Shares available for grant (in shares)	98.2

Stockholders_ (Deficit) Equit_5

Stockholders’ (Deficit) Equity - Schedule of Stock Option and Restricted Stock Activity (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Number of shares available for issuance under the Plans
Beginning balance (in shares)	95.2	78.5
Additional shares authorized (in shares)	18.8	20.3
Stock options assumed (in shares)		0.4
Options and restricted stock units and awards canceled (in shares)	6.9	11
Shares withheld related to net share settlement (in shares)	5.1	4.6
Options and restricted stock units and awards granted (in shares)	(27.8)	(19.6)
Ending balance (in shares)	98.2	95.2	78.5
Number of shares outstanding under the Plans
Beginning balance (in shares)	0.9	1.3
Stock options assumed (in shares)		0.4
Options exercised and restricted stock units and awards released (in shares)	(0.1)	(0.7)
Options and restricted stock units and awards canceled (in shares)	(0.4)	(0.1)
Ending balance (in shares)	0.4	0.9	1.3
Vested at end of period (in shares)	0.3
Unvested at end of period (in shares)	0.1
Weighted- average exercise price per share
Beginning balance (in dollars per share)	$ 12.09	$ 13.73
Stock options assumed (in dollars per share)		2.17
Options exercised and restricted stock units and awards released (in dollars per share)	3	9.77
Options and restricted stock units and awards canceled (in dollars per share)	18.53	11.84
Ending balance (in dollars per share)	11.30	$ 12.09	$ 13.73
Vested at end of period (in dollars per share)	13.83
Unvested at end of period (in dollars per share)	$ 2.01
Options outstanding, Weighted- average remaining contractual term (In years)
Weighted-average contractual term	4 years 6 months	5 years 4 months 24 days	5 years 8 months 12 days
Weighted-average contractual term, Vested at end of period	4 years 1 month 6 days
Options outstanding, aggregate intrinsic value	$ 4.5	$ 10	$ 11.4
Vested during period, aggregate intrinsic value	2.8
Unvested during period, aggregate intrinsic value	$ 1.7
DocSend Inc.
Number of shares outstanding under the Plans
Stock options assumed (in shares)	0.9
Restricted Stock
Restricted Stock Outstanding, Number of Plan shares outstanding
Beginning balance (in shares)	27.8	31.9
Options exercised and restricted stock units and awards released (in shares)	(14.3)	(12.7)
Options and restricted stock units and awards canceled (in shares)	(6.5)	(11)
Options and restricted stock units and awards granted (in shares)	27.8	19.6
Ending balance (in shares)	34.8	27.8	31.9
Vested at end of period (in shares)	0
Restricted Stock Outstanding, Weighted- average grant date fair value per share
Beginning balance (in dollars per share)	$ 24.17	$ 19.79
Options exercised and restricted stock units and awards released (in dollars per share)	23.37	20.77
Options and restricted stock units and awards canceled (in dollars per share)	23.72	21.12
Shares repurchased for tax withholdings on release of restricted stock (in dollars per share)	23.40	20.71
Options and restricted stock units and awards granted (in dollars per share)	22.68	26.34
Ending balance (in dollars per share)	23.40	$ 24.17	$ 19.79
Vested at end of period (in dollars per share)	0
Restricted Stock | DocSend Inc.
Restricted Stock Outstanding, Weighted- average grant date fair value per share
Stock options assumed (in dollars per share)	$ 26.86
Fair value of awards assumed in acquisition	$ 0.4

Stockholders_ (Deficit) Equit_6

Stockholders’ (Deficit) Equity - Schedule of Pre-Tax Intrinsic Value of Options Exercised (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Stockholders' Equity Note [Abstract]
Intrinsic value of options exercised	$ 2.9	$ 12.3

Stockholders_ (Deficit) Equit_7

Stockholders’ (Deficit) Equity - Assumed Stock Options (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock options assumed (in shares)		0.4
Dividend yield	0%
DocSend Inc.
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock options assumed (in shares)	0.9
Weighted average grant date fair value of stock options assumed (in dollars per share)	$ 25.28
Fair value of options assumed in business combination	$ 9.3
Post combination, stock-based compensation expense	$ 8.1

Stockholders_ (Deficit) Equit_8

Stockholders’ (Deficit) Equity - Fair Value of Stock Option Assumptions Used (Details)	12 Months Ended
	Dec. 31, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Dividend yield	0%
Employee Stock Option | DocSend Inc.
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expected volatility	47%
Risk-free interest rate, minimum	0.15%
Risk-free interest rate, maximum	1.29%
Dividend yield	0%
Employee Stock Option | Minimum | DocSend Inc.
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expected term (in years)	2 years
Employee Stock Option | Maximum | DocSend Inc.
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expected term (in years)	6 years 9 months 18 days

Stockholders_ (Deficit) Equit_9

Stockholders’ (Deficit) Equity - Co-Founder Grants (Details) - Restricted Stock shares in Millions, $ in Millions	1 Months Ended	3 Months Ended	12 Months Ended
	Dec. 31, 2017 tranche shares	Dec. 31, 2021 shares	Dec. 31, 2022 USD ($) shares	Dec. 31, 2021 USD ($) shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares granted (in shares)			27.8	19.6
Vesting period			4 years
Vested at end of period (in shares)			0
Co-Founder Grants
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expiration period	10 years
Number of tranches | tranche	9
Trading period	30 days
Stock-based compensation expense | $			$ 11.7	$ 14.6
Remaining unamortized stock-based compensation | $			$ 9.4
Co-Founder Grants | Tranche One
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting period	4 years
Co-Founder Grants | Tranche One | Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Percentage vested maximum	20%
Co-Founder Grants | Chief Executive Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares granted (in shares)	10.3
Vested at end of period (in shares)		2.1

Net Income (Loss) Per Share - S

Net Income (Loss) Per Share - Schedule of Earnings Per Share, Basic and Diluted (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Numerator
Net income (loss)	$ 553.2	$ 335.8	$ (256.3)
Weighted-average shares used in computing net income (loss) per share attributable to common stockholders, basic (in shares)	361.2	388	414.3
Net income (loss) per share, basic (in dollars per share)	$ 1.53	$ 0.87	$ (0.62)
Weighted-average number of common shares outstanding used in computing diluted net income per share (in shares)	363.3	395.8	414.3
Net income (loss) per share, diluted (in dollars per share)	$ 1.52	$ 0.85	$ (0.62)
Class A
Numerator
Net income (loss)	$ 426.8	$ 263.9	$ (182.5)
Weighted-average shares used in computing net income (loss) per share attributable to common stockholders, basic (in shares)	278.6	304.9	295
Net income (loss) per share, basic (in dollars per share)	$ 1.53	$ 0.87	$ (0.62)
Reallocation of net income as a result of conversion of Class B to Class A common stock	$ 126.4	$ 71.9
Reallocation of net income to Class B common stock	0	0
Net income attributable to common stockholders for diluted EPS	$ 553.2	$ 335.8
Weighted-average effect of dilutive restricted stock units and awards and employee stock options (in shares)	2.1	7.8
Conversion of Class B to Class A common stock (in shares)	82.6	83.1
Weighted-average number of common shares outstanding used in computing diluted net income per share (in shares)	363.3	395.8	295
Net income (loss) per share, diluted (in dollars per share)	$ 1.52	$ 0.85	$ (0.62)
Class B
Numerator
Net income (loss)	$ 126.4	$ 71.9	$ (73.8)
Weighted-average shares used in computing net income (loss) per share attributable to common stockholders, basic (in shares)	82.6	83.1	119.3
Net income (loss) per share, basic (in dollars per share)	$ 1.53	$ 0.87	$ (0.62)
Reallocation of net income as a result of conversion of Class B to Class A common stock	$ 0	$ 0
Reallocation of net income to Class B common stock	(0.7)	(1.3)
Net income attributable to common stockholders for diluted EPS	$ 125.7	$ 70.6
Weighted-average effect of dilutive restricted stock units and awards and employee stock options (in shares)	0	0.1
Conversion of Class B to Class A common stock (in shares)	0	0
Weighted-average number of common shares outstanding used in computing diluted net income per share (in shares)	82.6	83.2	119.3
Net income (loss) per share, diluted (in dollars per share)	$ 1.52	$ 0.85	$ (0.62)

Net Income (Loss) Per Share -_2

Net Income (Loss) Per Share - Schedule of Potentially Dilutive Securities Excluded from Computation (Details) - shares shares in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	104.6	75.6	22.7
Restricted stock units and awards
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	20.4	2.4	10.5
Options to purchase shares of common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	0.3	0.1	0.9
Co-Founder Grants
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	8.3	9.3	11.3
Convertible Senior Notes
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	37.8	31.9	0
Warrants
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share (in shares)	37.8	31.9	0

Income Taxes - Schedule of Loss

Income Taxes - Schedule of Loss from Continuing Operations Before Income Taxes (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income Tax Disclosure [Abstract]
Domestic	$ 37.8	$ 185.3	$ (57.7)
Foreign	154.9	114	(192.5)
Income (loss) before income taxes	$ 192.7	$ 299.3	$ (250.2)

Income Taxes - Components of In

Income Taxes - Components of Income Tax Expense (Benefit) (Details) - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Current:
Federal		$ (13.2)	$ (0.4)	$ 0
State		(15.3)	(0.7)	(2.7)
Foreign		(7.5)	(2.5)	(6)
Deferred:
Federal		386.7	2.2	0
State		30	0.4	0
Foreign		(20.2)	37.5	2.6
Benefit from (provision for) income taxes	[1]	$ 360.5	$ 36.5	$ (6.1)
[1]Results of Operations for the year-ended 2022 include a one-time benefit from income taxes of $420.2 million due to the release of a valuation allowance on the U.S. federal and certain state deferred tax assets. Results of Operations for the year-ended 2021 include a one-time benefit from income taxes of $38.1 million from the release of a valuation allowance on the Irish deferred tax assets.

Income Taxes - Income Tax Rate

Income Taxes - Income Tax Rate Reconciliation (Details) - USD ($) $ in Millions		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income Tax Disclosure [Abstract]
Tax (provision) benefit at federal statutory rate		$ (40.5)	$ (62.8)	$ 52.5
State taxes, net of federal benefit		(4.9)	(5.5)	1.2
Foreign rate differential		(34)	0.9	(12.2)
Research and other credits		45.3	38.1	34.9
Non-deductible compensation		(3.4)	(6.2)	(4.1)
Permanent differences		(1.8)	(0.8)	(1.8)
Change in valuation allowance		409.9	51.4	(69.6)
Stock-based compensation		(4.3)	23.5	(3.2)
Other non-deductible items		(5.8)	(2.1)	(3.8)
Benefit from (provision for) income taxes	[1]	$ 360.5	$ 36.5	$ (6.1)
[1]Results of Operations for the year-ended 2022 include a one-time benefit from income taxes of $420.2 million due to the release of a valuation allowance on the U.S. federal and certain state deferred tax assets. Results of Operations for the year-ended 2021 include a one-time benefit from income taxes of $38.1 million from the release of a valuation allowance on the Irish deferred tax assets.

Income Taxes - Components of De

Income Taxes - Components of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($) $ in Millions	Dec. 31, 2022	Dec. 31, 2021
Deferred tax assets:
Net operating loss carryforwards	$ 40.8	$ 202.6
Research credit carryforwards	268.9	263.9
Stock-based compensation	24.1	25.2
Accruals and reserves	36.8	41.6
Lease liability	141.8	168.4
Convertible senior notes	47.5	57.3
Capitalized research expenditures	123.9	0
Other	0.6	0
Gross deferred tax assets	684.4	759
Valuation allowance	(111.6)	(586.7)
Total deferred tax assets, net of valuation allowance	572.8	172.3
Deferred tax liabilities:
Fixed assets and intangible assets	14.4	20.6
Right-of-use assets	59.5	110.2
Other	0.2	0.3
Total deferred tax liability	74.1	131.1
Net deferred tax assets	$ 498.7	$ 41.2

Income Taxes - Additional Infor

Income Taxes - Additional Information (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Operating Loss Carryforwards [Line Items]
Benefit from income taxes related to valuation allowance	$ 420.2
Deferred tax asset realization adjustment	61.2
Valuation allowance increase (decrease)	(475.1)	$ 3
Research credit carryforwards	268.9	263.9
Unrecognized tax benefits	127.2	107.3	$ 91.4	$ 74.5
Unrecognized tax benefits that would impact effective tax rate	88.5
Unrecognized tax benefit that would result in adjustment to deferred tax assets	38.7
Penalties and interest accrued	5.3
Penalties and interest expense	1.7	$ 0.4	$ 0.7
Federal
Operating Loss Carryforwards [Line Items]
Operating loss carryforwards	13.3
Operating loss carryforwards, subject to expiration	7.8
Operating loss carryforwards, not subject to expiration	5.5
Research credit carryforwards	249.4
State
Operating Loss Carryforwards [Line Items]
Operating loss carryforwards	118.5
Research credit carryforwards	150.3
Foreign
Operating Loss Carryforwards [Line Items]
Operating loss carryforwards	150.3
Tax credit carryforward	0.5
Research Tax Credit Carryforward | Federal
Operating Loss Carryforwards [Line Items]
Unrecognized tax benefits	72.5
Research Tax Credit Carryforward | State
Operating Loss Carryforwards [Line Items]
Unrecognized tax benefits	38.7
State Enterprise Tax Credit Carryforward
Operating Loss Carryforwards [Line Items]
Tax credit carryforward	$ 3.6

Income Taxes - Reconciliation o

Income Taxes - Reconciliation of Unrecognized Tax Benefits (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Reconciliation of Unrecognized Tax Benefits, Excluding Amounts Pertaining to Examined Tax Returns [Roll Forward]
Balance of gross unrecognized tax benefits at the beginning of the fiscal year	$ 107.3	$ 91.4	$ 74.5
Gross increases related to prior period tax positions	0	0	1.3
Gross decreases related to prior period tax positions	0	(0.3)	0
Gross increases related to current period tax positions	20.3	18.5	15.8
Reductions due to lapse in statute of limitations	(0.4)	(1.5)	(0.2)
Reductions due to settlements with taxing authorities	0	(0.8)	0
Balance of gross unrecognized tax benefits at the end of the fiscal year	$ 127.2	$ 107.3	$ 91.4

Geographic Areas (Details)

Geographic Areas (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Segment Reporting Information [Line Items]
Property and equipment, net	$ 308.4	$ 322
Revenue	2,324.9	2,157.9	$ 1,913.9
United States
Segment Reporting Information [Line Items]
Property and equipment, net	300.2	316.6
Revenue	1,264.2	1,130	999.3
International
Segment Reporting Information [Line Items]
Property and equipment, net	8.2	5.4
Revenue	$ 1,060.7	$ 1,027.9	$ 914.6