SecProbe.io

March 22, 2011
 Via Email

 Patrick White Chief Executive Officer
Document Security Systems, Inc.
28 Main Street East, Suite 1525 Rochester, New York 14614
Re: Document Security Systems, Inc.
  Amendment No. 1 to Registra tion Statement on Form S-3
Filed March 7, 2011
  File No. 333-171940

Dear Mr. White:
 We have reviewed your response letter dated March 7, 2011 and the above-referenced
filing, and have the following comments.  Where prior comments are referenced, they refer to
our letter dated February 24, 2011.

General

 1. Your Forms 8-K filed on February 24, 2011 a nd March 17, 2011 disclose that the terms
of the unregistered offering were revised subseq uent to the date of your initial filing of
the resale registration statement covering the shares and shares underlying warrants
issued in the unregistered offering.  In your response letter, please provide us with a
detailed legal analysis explaining your comp liance with Sections 4(2) and 5 of the
Securities Act of 1933, and supporting your apparent  belief that the unregistered offering
was completed prior to your initial filing of  the resale registration statement.  For
guidance, refer to Questions 139.06 and 139.11 of the Division of Corporation Finance’s
Compliance and Disclosure Interpreta tions of Securities Act Sections.
 Prospectus Cover Page

 2. Please expand the first paragraph to disclose  that the 1,555,543 shares that are offered by
the selling security holder consist of 756,287 outstanding shares and 799,256 shares
underlying warrants.
 Selling Security Holder, page 13

 3. We reissue prior comment 5.  Notwithsta nding the limitation on the selling security
holder’s share ownership imposed by the purch ase agreement, it app ears that after the

Patrick White Document Security Systems, Inc. March 22, 2011 Page 2

 sale of shares in the offering, the selling secu rity holder will still bene ficially own at least
503,831 shares of common stock, which is appr oximately 2.6% of the company’s shares
outstanding as of March 4, 2011.  Please revise the table to in clude this disclosure.  See
Item 507 of Regulation S-K.
 Exhibit 5.1

 4. We reissue prior comment 10; the first paragrap h still refers to the registration of shares
of common stock “sold by the Company from time to time.”  Please ask counsel to revise
the first paragraph of its opi nion to reference the current resale offering by the selling
security holder.

Please contact Evan S. Jacobson at (202) 551-3428 or me at (202) 551-3462 with any
questions.
Sincerely,
   /s/ Mark P. Shuman
Mark P. Shuman
Branch Chief – Legal
 cc: Via Email

Gary A. Agron, Esq. Law Offices of Gary A. Agron