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Document
Security Systems, Inc.

200
Canal View Boulevard

Suite
300

Rochester,
NY 14623

Securities
and Exchange Commission

100
F Street N.E.

Washington,
D.C. 20549

Office
of Mergers and Acquisitions

Division
of Corporation Finance

Attention:
Christina Chalk

November
12, 2019

    Re:
    Document Security Systems, Inc.

    PRE 14A filed on November 4, 2019

    File No. 1-32146

Ladies
and Gentlemen:

Document
Security Systems, Inc. (the “Company”) is hereby submitting an Amendment to a Preliminary Proxy Statement on a Form
PREC14A (“Submission No. 2”). The Company previously submitted a Preliminary Proxy Statement on Form
PRE 14A on November 4, 2019 (“Submission No. 1”). Submission No. 2 has been revised to reflect the Company’s
responses to the comment letter to Submission No. 1 received on November 7, 2019 from the staff of the Commission (the “Staff”).

For
ease of review, we have set forth below each of the numbered comments of your letter in bold type followed by the Company’s
responses thereto. Unless otherwise indicated, capitalized terms used herein have the meanings assigned to them in Submission
No. 2 and all references to page numbers in such responses are to page numbers in Submission No. 2.

Preliminary
Proxy Statement filed on November 4, 2019

    1.
    Since this
    is a contested solicitation involving a director election contest, the correct EDGAR “tag” is PREC14A. Please
    revise in your next filing of the amended preliminary proxy statement.

    Response:
    The Company respectfully acknowledges the Staff’s comment and has reflected the correct EDGAR “tag” of PREC14A
    for Submission No. 2.

    2.
    Please mark
    the proxy statement as preliminary. See Rule 14a-6(e)(1).

    Response:
    The Company respectfully acknowledges the Staff’s comment and marked Submission No. 2 to reflect its filing as a preliminary
    proxy statement.

    3.
    Please fill
    in the blanks throughout the proxy statement. Information subject to change may be bracketed.

    Response:
    The Company respectfully acknowledges the Staff’s comment and has revised the disclosures throughout Submission No.
    2 to fill in all appropriate blanks. Information subject to change has been bracketed.

    4.
    Include a
    background section detailing the events and contacts with the dissidents leading up to this contest.

    Response:
    The Company respectfully acknowledges the Staff’s comment and included a background section of events and contacts with
    the dissidents in Submission No. 2.

Transactions
with Related Persons

    5.
    We note the
    disclosure that days before the record date for this annual meeting, the Company sold 6,000,000 additional shares to the Chairman
    of the Board, Fei Hang Chan. To present this sale in context, disclose the percentage increase in Mr. Chan’s holdings
    as a result of the November 1, 2019 purchase.

    Response:
The Company respectfully acknowledges the Staff’s comment and reflected in Submission No. 2 the percentage increase in Mr.
Chan’s holdings as a result of the November 1, 2019 purchase.

Proposal
1. Election of Directors

    6.
    For each of
    the nominees, provide dates for the positions listed that they have held over the last five years.

    Response:
    The Company respectfully acknowledges the Staff’s comment and reflected the biographical disclosures in Submission No.
    2 to address the Staff’s comment.

Form
of Proxy

    7.
    Please
    file a form of proxy card (marked preliminary) with your revised preliminary proxy statement

    Response:
    The Company respectfully acknowledges the Staff’s comment and has filed a form of proxy card (marked preliminary) with
    our revised proxy statement.

We
hope the foregoing answers are responsive to your comments. Please do not hesitate to contact our counsel, Jay Yamamoto, at (646)
810-0604 with any questions or comments regarding this correspondence.

    Sincerely,

    /s/
    Frank D. Heuszel

    Frank D .Heuszel

    cc:
    Jay Yamamoto, SRF LLP (via email)

    Wei
    Heng Fai Ambrose Chan, Document Security Systems, Inc. (via email)