424(B)(3) SUPPLEMENT REGISTRATION NO. 333-116317 SUPPLEMENT NO.2 DATED APRIL 28, 2005 TO PROSPECTUS DATED AUGUST 12, 2004 of DOCUMENT SECURITY SYSTEMS, INC. SELLING SHAREHOLDERS This prospectus supplement relates to the resale of an aggregate 3,000,000 shares of our common stock by certain of our shareholders. The selling shareholders own 1,565,000 shares of our common stock and warrants to purchase an additional 1,435,000 shares of common stock issuable to the Selling Security Holders upon exercise of warrants. You should read this prospectus supplement in conjunction with the prospectus dated August 12, 2004, which is to be delivered with this prospectus supplement. This prospectus supplement is qualified by reference to the prospectus except to the extent that the information herein contained supersedes the information contained in the prospectus. Capitalized terms used in this prospectus supplement and not otherwise defined herein have the meanings specified in the prospectus. Specifically, this Supplement No.2 relates to the transfer by Fordham Financial Management Inc. a selling shareholder, of an aggregate of warrants to purchase 359,150 shares of Common Stock, to the individuals listed below. The information in the following table is presented as of April 26, 2005 and supplements the information in the table appearing under the heading "Selling Security Holders" beginning on page 15 of the prospectus dated August 12, 2004, including any amendments or supplements thereto, and was provided by or on behalf of the selling security holders. The following table sets forth as to the Selling Security Holder listed below: The following list (or footnotes) provides: o the names of the selling shareholders. o the affiliation or material relationship we have, if any, with each selling shareholder. o the amount of shares beneficially owned by each selling shareholder before this offering. o the number of outstanding shares and shares underlying warrants being offered for each selling shareholder's account. Beneficial ownership includes shares owned and shares that the shareholder has the right to acquire within 60 days. Except as may be notes in a footnote below, all of the shares listed as underlying warrants are immediately acquirable and thus are beneficially owned by the selling shareholder holding the respective warrants. However, we have no control over when, if ever, a selling shareholder may exercise the option to exercise warrants held by such selling shareholder. SHARES CURRENTLY WARRANT SHARES BENEFICIALLY OUTSTANDING AND SHARES BEING TOTAL SHARES BEING OWNED BEFORE BEING REGISTERED IN REGISTERED IN REGISTERED IN NAME OF SELLING SHAREHOLDER OFFERING(1) OFFERING OFFERING OFFERING(4) - --------------------------- ----------- -------- -------- ----------- Fordham Financial Management, Inc. (2) 0 0 3,350 3,350 Karen Farrell (3) 0 0 3,350 3,350 David Goren (3) 0 0 3,350 3,350 Joseph Ingarra (3) 0 0 26,100 26,100 Bruce Inglis (3) 0 0 1,675 1,675 Mio Lum (3) 0 0 1,675 1,675 Mac Lutz (3) 0 0 3,350 3,350 Umberto Marcucci (3) 0 0 3,350 3,350 Peter Mazzone (3) 0 0 3,350 3,350 Fred Meyers (3) 0 0 6,700 6,700 Robert Sagarino (3) 0 0 26,800 26,800 John Stewart (3) 0 0 3,350 3,350 Vace Partners (3) 0 0 26,800 26,800 Eustace Conway (3) 0 0 3,350 3,350 John Young (3) 0 0 3,350 3,350 Janzig Demirkan (3) 0 0 3,350 3,350 Jay Belding (3) 0 0 3,350 3,350 William Baquet (3) 0 0 169,685 169,685 2 SHARES CURRENTLY WARRANT SHARES BENEFICIALLY OUTSTANDING AND SHARES BEING TOTAL SHARES BEING OWNED BEFORE BEING REGISTERED IN REGISTERED IN REGISTERED IN NAME OF SELLING SHAREHOLDER OFFERING(1) OFFERING OFFERING OFFERING(4) - --------------------------- ----------- -------- -------- ----------- Charles Giordano (3) 0 0 25,425 25,425 Dean Kajouras (3) 0 0 14,400 14,400 Rich Adams (3) 0 0 4,000 4,000 Jodi Mandarino (3) 0 0 200 200 Maria Luppino (3) 0 0 200 200 Jesus Ramos (3) 0 0 200 200 Joseph Priincipe (3) 0 0 500 500 Jason Barter (3) 0 0 200 200 Harvey Latzen (3) 0 0 3,000 3,000 Patricia DiDomenico (3) 0 0 200 200 Margaret Grennes (3) 0 0 300 300 Charles Giordano, Jr. (3) 0 0 2,000 2,000 Michael Natapov (3) 0 0 125 125 Matthew Cody (3) 0 0 250 250 John Lowry (3) 0 0 3,405 3,405 Josh Conroy (3) 0 0 1,125 1,125 Andrew Sidebotham (3) 0 0 375 375 Stephen Liotta (3) 0 0 1,250 1,250 Chiaki Yamamoto (3) 0 0 500 500 George Carris (3) 0 0 4,405 4,405 3 SHARES CURRENTLY WARRANT SHARES BENEFICIALLY OUTSTANDING AND SHARES BEING TOTAL SHARES BEING OWNED BEFORE BEING REGISTERED IN REGISTERED IN REGISTERED IN NAME OF SELLING SHAREHOLDER OFFERING(1) OFFERING OFFERING OFFERING(4) - --------------------------- ----------- -------- -------- ----------- Adam Bush (3) 0 0 125 125 John Gino (3) 0 0 135 135 William Barbour (3) 0 0 1,375 1,375 Preston Kassem (3) 0 0 2,530 2,530 Total 0 0 362,500 362,500 - ------------------- (1) Figures include the shares of Common Stock and shares underlying warrants being registered in the registration statement of which this prospectus forms a part. (2) Fordham Financial Management Inc. served as placement agent in connection with the private placement offering recently completed by the Company in which the Company raised $5,800,000 in gross proceeds. The private offering was completed in December 2003. Fordham Financial is an NASD member brokerage firm. Fordham Financial received 362,500 warrants as compensation for its services as placement agent. The warrants have an exercise price of $4.80 per share. The warrants expire on November 29, 2008. Fordham Financial is a registered broker dealer and is controlled by William Baquette, who has the control and power to vote and/or sell the securities (3) The named selling shareholder may be deemed an associated person of a registered broker dealer firm under the rules of the SEC and NASD. Further, based upon information provided to us by the selling shareholder, we have been advised that at the time of purchase, there were no agreements or understandings, directly or indirectly, with any person to distribute the securities held by the selling shareholder. Document Security Systems has no arrangements or understandings with any persons, including any broker dealer firm, to distribute the securities. The named selling shareholder is an employee of Fordham Financial Management, an NASD member firm. (4) The number of shares which may be resold by the selling shareholder assumes the sale of all shares of common stock and shares underlying warrants. The registration statement of which this Prospectus forms a part includes additional shares pursuant to SEC Rule 416 which may be required to be issued pursuant to the anti-dilution provisions of the warrants for stock splits, stock dividends and similar corporate transaction. 4