Convertible Senior Notes | Debt Our debt consists of the following as of March 31, 2023 and December 31, 2022 (in thousands): March 31, 2023 December 31, 2022 Revolving Credit Facility $ 48,500 $ 46,500 Principal amount of Convertible Senior Notes 77,063 75,000 Unamortized debt issuance costs (1,020) (1,231) Net carrying amount 76,043 73,769 Total debt $ 124,543 $ 120,269 Interest expense, net for the three months ended March 31, 2023 and 2022 was as follows (in thousands): Three Months Ended March 31, 2023 2022 Interest expense on Revolving Credit Facility $ 1,196 $ — Interest expense on Convertible Senior Notes 1,206 938 Amortization of debt issuance costs 211 194 Other, net (23) (1) Total interest expense, net $ 2,590 $ 1,131 Interest accrued but not paid as of March 31, 2023 and December 31, 2022 totaled $3.8 million and $3.5 million, respectively, and is included within accrued expenses in the condensed consolidated balance sheets. Revolving Credit Facility On April 26, 2022, Legacy Appgate, Appgate, the other guarantors party thereto and SIS Holdings entered into a revolving credit agreement (the “Revolving Credit Agreement”) which provides for a $50.0 million unsecured, revolving credit facility (the “Revolving Credit Facility”). This indebtedness is contractually subordinated to the Convertible Senior Notes and matures on the earlier to occur of (a) June 30, 2023, (b) the closing of a registered offering of Capital Stock (as defined in the Revolving Credit Agreement) of the Company in an aggregate amount equal to $50.0 million or more and (c) the date of which the Loans (as defined in the Revolving Credit Agreement) are accelerated upon an Event of Default (as defined in the Revolving Credit Agreement). Interest accrues on amounts drawn under the Revolving Credit Facility at a rate of 10.0% per annum, payable in cash on the Final Maturity Date (as defined in the Revolving Credit Agreement). All obligations under the Revolving Credit Agreement are guaranteed by Appgate and Legacy Appgate’s domestic subsidiaries. The Revolving Credit Agreement is subject to customary terms, covenants and conditions. Those covenants include restrictions on our ability to, among other things, incur additional debt and issue disqualified stock; create liens; pay dividends, acquire shares of capital stock, or make certain investments; issue guarantees; sell certain assets and enter into transactions with affiliates. The Revolving Credit Agreement also contains a financial covenant that requires that we maintain liquidity of not less than $10.0 million as of the last day of each calendar month. As of March 31, 2023, the Company had $7.8 million in cash and cash equivalents, and on March 31, 2023, SIS Holdings waived the Company’s noncompliance with the above-mentioned liquidity financial covenant with respect to the last day of March 2023. During the three months ended March 31, 2023, we borrowed $2.0 million under the Revolving Credit Facility, all of which remained outstanding as of March 31, 2023, and, when aggregated with the $46.5 million previously borrowed in 2022, resulted in a total of $48.5 million outstanding as of March 31, 2023. Convertible Senior Notes On February 9, 2021, Legacy Appgate issued $50.0 million in aggregate principal amount of convertible senior notes due 2024 (the “Initial Convertible Senior Notes”) to various funds managed by Magnetar Financial LLC (“Magnetar”). In connection with the closing of the merger of Newtown Merger Sub. Corp. (“Merger Sub”) with and into Legacy Appgate, with Legacy Appgate surviving and becoming a wholly owned subsidiary of Appgate (the “Merger”), Legacy Appgate issued an additional $25.0 million in aggregate principal balance in convertible notes to various funds managed by Magnetar (the “Additional Convertible Senior Notes” and together with the Initial Convertible Senior Notes and any PIK Notes (as defined below), the “Convertible Senior Notes”). The Convertible Senior Notes are subject to the terms and conditions of the note issuance agreement (the “Note Issuance Agreement”) among Legacy Appgate, Legacy Appgate’s wholly owned domestic subsidiaries and Magnetar, in its capacity as the representative (the “Representative”) of the holders of the Convertible Senior Notes (the “Noteholders”), and the note purchase agreement among Legacy Appgate and the Noteholders (the “Note Purchase Agreement”). Capitalized terms not otherwise defined in this Note 8 have the meanings ascribed to them in the Note Issuance Agreement. We received net proceeds of $72.8 million from the issuance of the Initial Convertible Senior Notes and Additional Convertible Senior Notes, after deducting fees and expenses of $2.2 million. We recorded these fees and expenses as debt issuance costs that will be amortized over the term of the Convertible Senior Notes. The Convertible Senior Notes are senior, unsecured obligations of Legacy Appgate, and the payment of the principal and interest is unconditionally guaranteed, jointly and severally by Legacy Appgate’s U.S. subsidiaries and, as of the closing of the Merger, also by Appgate. The Convertible Senior Notes will mature on February 9, 2024, unless earlier converted, redeemed, or repurchased. Interest on the Convertible Senior Notes is payable either entirely in cash or entirely in kind (“PIK Interest”), or a combination of cash and PIK Interest at our discretion. The Convertible Senior Notes bear interest at the annual rate of 5% with respect to interest payments made in cash and 5.50% with respect to PIK Interest, with interest payable semi-annually on February 1 and August 1 of each year, commencing on August 1, 2021. Additional notes (“PIK Notes”) to be issued for PIK Interest will have the same terms and conditions as the Convertible Senior Notes. On February 1, 2023, Legacy Appgate issued approximately $2.1 million in PIK Notes with respect to a single interest payment date. The Note Issuance Agreement includes certain affirmative and financial covenants we are required to satisfy (as further described below). Supplemental Agreement On October 12, 2021, in connection with the closing of the Merger, Appgate (which at the time was Newtown Lane Marketing, Incorporated (“Newtown Lane”)) entered into a supplemental agreement (the “Supplemental Agreement”) with Legacy Appgate and Magnetar, as Representative of the Noteholders, pursuant to which Appgate, among other things, unconditionally guaranteed all of Legacy Appgate’s Obligations under the Note Issuance Agreement, including the Convertible Senior Notes, and assumed all of Legacy Appgate’s Conversion Obligations and Change of Control Conversion Obligations under the Note Issuance Agreement. Amendment to Note Purchase Agreement and Note Issuance Agreement and Waiver to Note Purchase Agreement and Registration Rights Agreement As of February 9, 2022, the Company, Legacy Appgate, the Noteholders and the Representative entered into an Amendment to Note Purchase Agreement and Note Issuance Agreement and Waiver to Note Purchase Agreement and Registration Rights Agreement (the “Amendment and Waiver”). The Amendment and Waiver modified: (i) the Note Purchase Agreement by (a) (1) extending the date by which the Representative or its affiliates may elect to consummate an Optional Closing (as defined in the Note Purchase Agreement) until the earlier of (x) 75 days after the Company closes a registered offering of equity securities in an aggregate amount of no less than $40.0 million and (y) October 31, 2022 and (2) requiring the Company’s consent to effect any Optional Closing, and (b) waiving, for the period of time set forth in the Amendment and Waiver, certain registration rights of the Noteholders; (ii) the Note Issuance Agreement to provide for the incurrence of certain subordinated indebtedness; and (iii) that certain Registration Rights Agreement (the “Registration Rights Agreement”), dated as of February 8, 2021 entered into by and among Legacy Appgate and the Noteholders, by waiving, for the period of time set forth in the Amendment and Waiver, certain registration rights of the Noteholders. The period in which the Representative could have elected to consummate an Optional Closing has since expired and no additional Convertible Senior Notes were issued in an Optional Closing. As of October 14, 2022, the Company, Legacy Appgate, the Noteholders and the Representative entered into an additional Waiver to Note Purchase Agreement and Registration Rights Agreement (the “Second Waiver”) to extend the waiver by the Noteholders of certain registration rights pursuant to the Amendment and Waiver for the additional period set forth in the Second Waiver. As of January 24, 2023, the Company, Legacy Appgate, the Noteholders and the Representative entered into an additional Waiver to Note Purchase Agreement and Registration Rights Agreement (the “Third Waiver”) to extend the waiver by the Noteholders of certain registration rights pursuant to the Amendment and Waiver for the additional period set forth in the Third Waiver. Other key terms of the Convertible Senior Notes, as of March 31, 2023, were as follows: Conversion upon Change of Control. If Legacy Appgate undergoes a Change of Control other than the Merger prior to maturity, each holder of Convertible Senior Notes shall have the option to convert all or any portion of such Convertible Senior Notes into Legacy Appgate common stock or, following entry into the Supplemental Agreement (as defined above), our common stock, subject to and in accordance with the terms of the Note Issuance Agreement, including the applicable conversion rate thereunder. Conversion . Other than upon a Change of Control, prior to maturity, each holder of the Convertible Senior Notes shall have the option to convert all or any portion of such Convertible Senior Notes into Legacy Appgate common stock or, following entry into the Supplemental Agreement, our common stock, subject to and in accordance with the terms of the Note Issuance Agreement, including the applicable conversion rate thereunder. Guarantees; Conversion Obligations. The Convertible Senior Notes are guaranteed by each of Legacy Appgate’s wholly owned domestic subsidiaries and, as of the closing of the Merger, also by Appgate. Upon the consummation of certain events resulting in Legacy Appgate becoming a direct or indirect subsidiary of any person (including the Merger), such acquiring person, any direct or indirect parent company thereof and each subsidiary thereof (immediately prior to such event) shall unconditionally guarantee Legacy Appgate’s Obligations and assume all of Legacy Appgate’s Conversion Obligations and Change of Control Conversion Obligations and, upon such assumption, Legacy Appgate shall be released from its Conversion Obligations and Change of Control Conversion Obligations. Repurchase Upon a Fundamental Change. Upon the occurrence of a Fundamental Change at any time after a Public Company Event, each holder of Convertible Senior Notes shall have the option to require Legacy Appgate to repurchase for cash all or any portion of such Convertible Senior Notes, at a repurchase price equal to 100% of the principal amount thereof, plus accrued and unpaid interest thereon, subject to and in accordance with the terms of the Note Issuance Agreement. Repurchase Upon a Change of Control. Upon the occurrence of a Change of Control, each holder of Convertible Senior Notes shall have the option to require Legacy Appgate to repurchase for cash all or any portion of such Convertible Senior Notes, at a repurchase price equal to 102% of the principal amount thereof, plus accrued and unpaid interest thereon, subject to and in accordance with the terms of the Note Issuance Agreement. Covenants. The Note Issuance Agreement contains restrictive covenants that, among other things, generally limit the ability of our and certain of our subsidiaries (subject to certain exceptions) to: (i) incur additional debt and issue Disqualified Stock; (ii) create liens; (iii) pay dividends, acquire shares of capital stock, or make investments; (iv) issue guarantees; (v) sell assets and (vi) enter into transactions with affiliates. The Note Issuance Agreement also contains a financial covenant that requires that we maintain liquidity of not less than $10.0 million as of the last day of each calendar month. As of March 31, 2023, the Company had $7.8 million in cash and cash equivalents, and on March 31, 2023, the Representative and the Noteholders waived the Company’s noncompliance with the above-mentioned liquidity financial covenant with respect to the last day of March 2023. The foregoing restrictive covenants are subject to a number of important exceptions and qualifications, as set forth in the Note Issuance Agreement. Events of Default. The Note Issuance Agreement provides for customary events of default which include (subject in certain cases to customary grace and cure periods), among others: (i) nonpayment of principal or interest; (ii) breach of covenants or other agreements in the Note Issuance Agreement; (iii) defaults in failure to pay certain other indebtedness; and (iv) certain events of bankruptcy or insolvency. Generally, if an event of default occurs and is continuing under the Note Issuance Agreement, Magnetar or the holders of at least 25% in aggregate principal amount of the Convertible Senior Notes then outstanding may declare the principal of, premium, if any, and accrued interest on all the Convertible Senior Notes immediately due and payable. No Registration. The Convertible Senior Notes and any Appgate common stock to be issued upon conversion of the Convertible Senior Notes have not been registered under the Securities Act of 1933, as amended (the “Securities Act”), or any state securities laws and may not be offered or sold in the United States absent registration under the Securities Act or an applicable exemption from registration requirements. This description of the Note Issuance Agreement and the Convertible Senior Notes does not constitute an offer to sell, or the solicitation of an offer to buy, any securities and shall not constitute an offer, solicitation or sale in any jurisdiction in which such offer, solicitation or sale would be unlawful. If the holders have not converted the Convertible Senior Notes and the Convertible Senior Notes have not been redeemed by the maturity date, Legacy Appgate must repay the outstanding principal amount and accrued interest. Embedded Derivative Liability The Convertible Senior Notes contain (i) call options to be settled in cash upon the occurrence of a Change of Control (other than the Merger), (ii) put options to be settled in cash contingent upon the occurrence of a Fundamental Change after a Public Company Event or a Change of Control (other than the Merger) and (iii) a default interest rate increase of 1.5% applicable upon the occurrence of an event of default. Appgate evaluated these embedded redemption features under the guidance of ASC 815, Derivatives and Hedging , and determined that a redemption feature contained a substantial premium requiring bifurcation at fair value. However, management determined the probability of a Change of Control to be remote and as such the fair value of the embedded redemption feature has been estimated to be zero. Management also evaluated the contingent interest feature and determined the likelihood of payment to be remote. Accordingly, the fair value of the contingent interest feature was also estimated to be zero. Lastly, management evaluated the embedded conversion feature, and determined that following the closing of the Merger, this embedded feature meets the net settlement criterion under ASC 815-15-25. Consequently, the automatic conversion meets the criteria under ASC 815-15-25-1(c). For an embedded feature to be bifurcated, it must meet all three criteria in ASC 815-15-25-1. Therefore, this embedded feature requires bifurcation. Accordingly, we have recorded an embedded derivative liability representing the combined fair value of the right of the Noteholders to receive 11,284,833 shares of our common stock upon conversion of the Convertible Senior Notes at any time (the “conversion feature”). The embedded derivative liability is presented as a liability in our condensed consolidated balance sheet and is adjusted to reflect fair value at each period end with changes in fair value recorded in the “Change in fair value of embedded derivative liability” financial statement line item of our condensed consolidated statements of operations. We will continue to adjust the embedded derivative liability for changes in fair value until the underlying conversion feature is exercised, redeemed, cancelled or expires. As of March 31, 2023 and December 31, 2022, the carrying amount of this embedded derivative included in our condensed consolidated balance sheets was $0.1 million and $19.7 million, respectively. The fair value of this derivative is estimated using Level 3 inputs in the fair value hierarchy on a recurring basis. Refer to Note 4 – Financial Instruments and Fair Value Measurements . Based on the estimated value of the derivative at March 31, 2023, if the Noteholders were to exercise the conversion feature, they would not receive any excess over the aggregate principal amount on the Convertible Senior Notes. |