SecProbe.io

February 8, 2013

Via E -Mail
Robert Bzdick
Chief Executive Officer
Document Security Systems, Inc.
First Federal Plaza
28 Main Street East, Suite 1525
Rochester, NY 14614

Re: Document Security Systems, Inc.
Amendment No. 1 to Registration Statement on Form S -4
Filed January 15, 2013
File No. 333-185134

Dear Mr. Bzdick :

We have reviewed your  amended filing and your response letter dated January 15, 2013
and have the following comments .  Unless otherwise not ed, references to prior  comments  refer to
our comment letter dated December 28, 2012.

General

1. We are in receipt of your request for confidential treatment for portions of Exhibit 10.72
submitted in a separate application pursuant to Securities Act Rule 406.  We will respond
your request for confidential treatment under separate cover.  Please be ad vised that all
comments relating to your confidential treatment request must be resolved prior to
effectiveness of your registration statement on Form S -4.

2. We note your responses to prior comments 3, 4 and 5 of our prior letter.  It is our
understanding that the total number of Document Security Systems, Inc. (“DSS”)
common stock to be issued as part of this registration statement will be up to 27, 350,000
shares consisting of the following:
 up to 17,250,000 DSS common stock shares exchanged for Lexington common
and preferred stock;
 7,100,000 DSS common stock shares held in escrow; and
 up to 3,000,000 DSS common stock shares issued if Lexington’s cash balance
exceeds $7.5 million.
In addition, it appears that you seek to register:
 2,000,000 DSS options an d 2,000,000 shares of DSS common stock underlying
those options;

Robert Bzdick
Document Security Systems, Inc.
February 8, 2013
Page 2

  4,859,894 warrants with an exercise price of $4.80 per share and the 4,859,894
shares of DSS common stock underlying the warrants; and
 additional DSS convertible preferred stock or warrants with an exercise price for
$.02 per share if any Lexington preferred stockholder will become a 9.99% or
more beneficial owner of DSS common sto ck as a result of this merger.

To the extent this  summary  accurately reflects your transaction, please revise your
prospectus cover page, questions and answers, and summary term sheet to make this clear
in narrative or tabular form.  Alternatively, please provide further clarification.

 Prospectus Cover Page

3. We note the illustrative examples on pages 1 -3, 15 -16, and 65 -66 demonstrating the
mechanics of how an individual stockholder may be affected by the various exchange
ratios; however, this presentation, while useful, is too dense for inclusion on the
prospectus cover page.  Please substantially revise your prospectus c over page to limit the
information to the key features of the transaction.  Please note that you may include, as
appropriate, cross -references to sections within your prospectus that contain more
detailed explanations.  In this regard, we note that your re vised dis closures on pages 1 -3
and 15 -16 should also include specific cross -references to more detailed disclosure
regarding how the number of securities to be issued for each Lexington security holder
will be determined.  In addition, please replace the repeated generic statement “as
described in this proxy s tatement/prospectus” with cross -references to specific sections or
pages where this information is available.

DSS Proposal No. 3: Approval of an Amendment to DSS’s Amended  and Restated Certificate of
Incorporation to Implement a Stagge red Board of Directors, page 104

4. We note your response to prior comment 8 regarding the identity of your prospective
board.  Please revise to disclose the names of the directors that will be  appointed, if
known, should the merger be approved and the staggered board proposal rejected.

You may contact Edwin Kim, Attorney -Advisor, at (202) 551 -3297 or, in his absence, me
at (202) 551 -3457 with any questions relating to your registration state ment.

Sincerely,

 /s/ Maryse Mills -Apenteng

 Maryse Mills -Apenteng
 Special Counsel

cc:  Via E -Mail
 Philip Jones, C hief Financial Officer

Robert Bzdick
Document Security Systems, Inc.
February 8, 2013
Page 3

 Document Security Systems, Inc.