Document:

Exhibit 4.1

                               TRIDEX CORPORATION
                           PROGRESSIVE SOFTWARE, INC.
                         ULTIMATE TECHNOLOGY CORPORATION
                                 61 Wilton Road
                           Westport, Connecticut 06880

                                                               February 18, 2000

MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY
MASSMUTUAL CORPORATE INVESTORS
MASSMUTUAL PARTICIPATION INVESTORS
MASSMUTUAL CORPORATE VALUE PARTNERS LIMITED
1295 State Street
Springfield, Massachusetts  01111

      Re: Fifth Amendment to Securities Purchase Agreements

Ladies and Gentlemen:

      TRIDEX CORPORATION, a Connecticut corporation (the "Holding Company"),
PROGRESSIVE SOFTWARE, INC., a North Carolina corporation and successor to Tridex
NC, Inc. ("PSI"), and ULTIMATE TECHNOLOGY CORPORATION, a New York corporation
("UTC") (the Holding Company, PSI, and UTC are sometimes collectively referred
to herein as the "Issuers" and each as an "Issuer"), jointly and severally agree
with each of you as follows.

                                   Background:

      A. Reference is made to those certain Securities Purchase Agreements dated
April 17, 1998, as amended by that certain letter of waiver and limited
amendment dated November 12, 1998 relating thereto, as further amended by that
certain Second Amendment to Securities Purchase Agreements dated March 26, 1999
(the "Second Amendment"), as further amended by that certain Third Amendment to
Securities Purchase Agreement dated June 30, 1999, and as further amended by
that certain Fourth Amendment to Securities Purchase Agreements dated September
30, 1999 (as so amended, the "Securities Purchase Agreements"), among the
Issuers and each of you. Capitalized terms used herein without definition have
the meanings ascribed to them in the Securities Purchase Agreements.

      B. The Issuers have requested that the holders of the Securities approve
certain amendments to and waivers under the Securities Purchase Agreements and
the other Operative Documents in connection with the Amendment No. 5 to Credit
Agreement dated as of February 18, 2000 (the "Fifth Amendment to Fleet Bank
Agreement") among the Holding Company, PSI, UTC, and Fleet National Bank,
pursuant to which certain amendments are being made to the Fleet Bank Documents
and Fleet National Bank is agreeing to the deferral of certain payments of
principal thereunder.

1. Consents and Waivers. Each of you hereby agrees that (a) the Issuers may
defer the payment of each of the April 17, 1999, July 17, 1999, October 17,
1999, January 17, 2000, April 17, 2000, July 17, 2000 and October 17, 2000
interest payments on the Notes and any scheduled principal or other payments in
respect of

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<PAGE>

the Notes until the earlier of January 1, 2001 or the sale of the capital stock
or assets of the Holding Company or PSI, at which date all such interest
payments on the Notes shall be due and payable in full together with the entire
outstanding principal amount of the Notes and all other amounts due in respect
of the Notes; and (b) notwithstanding anything to the contrary in the Securities
Purchase Agreements, the Issuers' failure to comply with section 13.6 of the
Securities Purchase Agreements prior to the date of this Fifth Amendment in
respect of the period ending December 31, 1998, shall not constitute an Event of
Default and the holders hereby waive any such Event of Default which existed for
such period prior to the date of this Fifth Amendment, provided that such
section 13.6 of the Securities Purchase Agreements as amended by the Second
Amendment shall only remain in effect in respect of periods ending subsequent to
December 31, 1998, and prior to January 1, 2001. As of January 1, 2001, such
section 13.6, as in effect prior to the date of the Second Amendment, shall be
deemed reinstated.

2. Conditions to Effectiveness of Fifth Amendment. This Fifth Amendment shall be
effective upon the first date upon which the following conditions shall have
been satisfied to your reasonable satisfaction:

      (a) The Issuers shall have delivered to you executed copies of each of the
following documents in form and substance satisfactory to you:

            (i) a fully executed counterpart of this Fifth Amendment;

            (ii) certified copies of (A) the resolutions of the Board of
      Directors of each of the Issuers approving this Fifth Amendment and the
      matters contemplated hereby and (B) all documents evidencing other
      necessary corporate actions and governmental approvals, if any, with
      respect to this Fifth Amendment and the other documents to be delivered
      hereunder;

            (iii) a certificate of the Secretary or an Assistant Secretary of
      each of the Issuers certifying the names and true signatures of the
      officers of each Issuer authorized to sign this Fifth Amendment and the
      other documents to be delivered hereunder;

            (iv) a schedule setting forth the uses of all proceeds of the sale
      of all of the capital stock of UTC on the date hereof;

            (v) projections prepared in good faith and based upon assumptions
      that the Holding Company believes are reasonable and take into account all
      material information regarding the matters set forth therein and
      representing the Holding Company's current estimate of the future
      financial performance of the Holding Company and its Subsidiaries;

            (vi) an opinion, dated the date hereof, from Messrs. Hinckley, Allen
      & Snyder LLP, counsel for the Issuers, substantially in the form of
      Exhibit 2(a)(vi) attached hereto; and

            (vii) an executed counterpart of the Fifth Amendment to Fleet Bank
      Agreement, substantially in the form of Exhibit 2(a)(vii) attached hereto.

      (b) The Issuers shall have paid in full all fees, expenses and
disbursements incurred by you in connection with this Fifth Amendment,
including, without limitation, the fees, expenses and disbursements of your
special counsel.

2.1 Conditions Subsequent. Within seven (7) days after the date of this Fifth
Amendment, the Issuers shall have deliver to you executed copies of each of the
following documents in form and substance satisfactory to you:

            (a) replacement Notes substantially in the form of Exhibit 2.1(a)
      attached hereto, which replacement Notes shall evidence the change in
      maturity of the outstanding Notes to January 1, 2001,

                                       2
<PAGE>

      and letters from Standard & Poor's assigning new private placement numbers
      to the replacement Notes;

            (b) a stock pledge agreement substantially in the form of Exhibit
      2.1(b) attached hereto (the "Pledge Agreement") evidencing a pledge of and
      perfected security interest (subject only to Liens permitted by section
      13.8 of the Securities Purchase Agreements, including, without limitation,
      the pledge of and first priority perfected security interest evidenced by
      the Fleet Bank Documents) in all of the shares of capital stock of PSI;
      and in all of the membership interests of Digital Restaurant Solutions,
      LLC.

3. No Default, Representations and Warranties, Etc.

      (a) The Issuers represent and warrant that the representations and
warranties contained in the Securities Purchase Agreements and the other
Operative Documents are in all material respects correct on and as of the date
hereof (after giving effect hereto) as if made on such date (except as a result
of transactions permitted under the Securities Purchase Agreements), that no
Default or Event of Default exists (other than those which have been
specifically waived pursuant to section 1 hereof) and that no condition exists
which has resulted in, or could reasonably be expected to result in, a Material
Adverse Change.

      (b) Each of the Issuers ratifies and confirms the Securities Purchase
Agreements and each of the other Operative Documents to which it is a party and
agrees that, after giving effect to the amendments, modifications and
supplements effected hereby, each such agreement, document and instrument is in
full force and effect, that its obligations thereunder and under this Fifth
Amendment are its legal, valid and binding obligations enforceable against it in
accordance with the terms thereof and hereof and that it has no defense, whether
legal or equitable, setoff or counterclaim to the payment and performance of
such obligations.

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<PAGE>

      (c) The Issuers agree that (i) if any default shall be made in the
performance or observation of any covenant, agreement or condition contained
herein or (ii) if any representation or warranty made by any Issuer herein or
therein shall prove to have been false or incorrect on the date as of which
made, the same shall constitute an Event of Default under the Securities
Purchase Agreements and the other Operative Documents and, in such event, you
and each other holder of any of the Securities shall have all rights and
remedies provided by law and/or provided or referred to in the Securities
Purchase Agreements and the other Operative Documents. The Issuers further agree
that this Fifth Amendment is an Operative Document and all references thereto in
the Securities Purchase Agreements and in any other of the Operative Documents
shall include this Fifth Amendment.

4. Payment of Transaction Costs. Without limiting the generality of the
provisions of the Operative Documents, the Issuers jointly and severally shall
pay all reasonable fees and disbursements incurred by you in connection
herewith, including, without limitation, the reasonable fees, expenses and
disbursements of your special counsel.

5. Governing Law. This Fifth Amendment, including the validity hereof and the
rights and obligations of the parties hereunder, shall be construed in
accordance with and governed by the domestic substantive laws of The
Commonwealth of Massachusetts without giving effect to any choice of law or
conflicts of law provision or rule that would cause the application of the
domestic substantive laws of any other jurisdiction.

6. Miscellaneous. The headings in this Fifth Amendment are for purposes of
reference only and shall not limit or otherwise affect the meaning hereof. This
Fifth Amendment embodies the entire agreement and understanding among the
parties hereto and supersedes all prior agreements and understandings relating
to the subject matter hereof. In case any provision in this Fifth Amendment
shall be invalid, illegal or unenforceable, the validity, legality and
enforceability of the remaining provisions shall not in any way be affected or
impaired thereby. This Fifth Amendment may be executed in any number of
counterparts and by the parties hereto on separate counterparts but all such
counterparts shall together constitute but one and the same instrument. Except
as specifically amended or modified pursuant to this Fifth Amendment, the
Securities Purchase Agreements shall remain in full force and effect, and the
execution and delivery of this Fifth Amendment shall not, except as expressly
provided herein, operate as a waiver of any of your rights, powers, or remedies
under the Securities Purchase Agreements or the documents and instruments
delivered in connection therewith.

           [The remainder of this page is left blank intentionally.]

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<PAGE>

      If you are in agreement with the foregoing, please sign the form of
agreement on the accompanying counterpart hereof, whereupon this Fifth Amendment
shall become a binding agreement under seal among the parties hereto. Please
then return one of such counterparts to the Issuers.

                                            Very truly yours,

                                            TRIDEX CORPORATION

                                            By /s/ Seth M. Lukash
                                               ------------------
                                                                         (Title)

                                            PROGRESSIVE SOFTWARE, INC.

                                            By /s/ George T. Crandall
                                               ----------------------
                                                                         (Title)

                                            ULTIMATE TECHNOLOGY CORPORATION

                                            By /s/ George T. Crandall
                                               ----------------------
                                                                         (Title)

The foregoing is hereby accepted and agreed to.

MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY

By: David L. Babson and Company Incorporated, its Investment Adviser

By /s/ Mark A. Ahmed
   -----------------
                    (Title)

                                       5
<PAGE>

MASSMUTUAL CORPORATE INVESTORS

By /s/ Charles C. McCobb, Chief Financial Officer
   ----------------------------------------------
                      (Title)

The foregoing is executed on behalf of MassMutual Corporate Investors, organized
under a Declaration of Trust, dated September 13, 1985, as amended from time to
time. The obligations of such Trust are not personally binding upon, nor shall
resort be had to the property of, any of the Trustees, shareholders, officers,
employees, or agents of such Trust, but the Trust's property only shall be
bound.

MASSMUTUAL PARTICIPATION INVESTORS

By /s/ Charles C. McCobb, Chief Financial Officer
   ----------------------------------------------
                      (Title)

The foregoing is executed on behalf of MassMutual Participation Investors,
organized under a Declaration of Trust, dated April 7, 1988, as amended from
time to time. The obligations of such Trust are not personally binding upon, nor
shall resort be had to the property of, any of the Trustees, shareholders,
officers, employees, or agents of such Trust, but the Trust's property only
shall be bound.

MASSMUTUAL CORPORATE VALUE PARTNERS LIMITED

By:   David L. Babson and Company Incorporated, under delegated authority from
      Massachusetts Mutual Life Insurance Company, its Investment Manager

By /s/ Mark A. Ahmed
   -----------------
                    (Title)

                                       6Exhibit 4.2

                               TRIDEX CORPORATION
                           PROGRESSIVE SOFTWARE, INC.
                         ULTIMATE TECHNOLOGY CORPORATION
                                 61 Wilton Road
                           Westport, Connecticut 06880

                                                February 18, 2000

MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY
MASSMUTUAL CORPORATE INVESTORS
MASSMUTUAL PARTICIPATION INVESTORS
MASSMUTUAL CORPORATE VALUE PARTNERS LIMITED
1295 State Street
Springfield, Massachusetts  01111

      Re: Fifth Amendment to Securities Purchase Agreements

      Reference is made to that certain Fifth Agreement to Securities Purchase
Agreements, a copy of which is attached hereto (the "Fifth Amendment"). Terms
used herein and not otherwise defined shall have the same meanings herein as
provided in the Fifth Amendment. This letter will evidence the agreement of the
Holding Company and PSI that the date "January 1, 2001" set forth in Sections
1(a) and 2.1(a) of the Fifth Amendment is hereby deleted and replaced with the
date "December 31, 2000."

<PAGE>

      If you are in agreement with the foregoing, please sign the form of
agreement on the accompanying counterpart hereof, whereupon this letter shall
become a binding agreement under seal among the parties hereto. Please then
return one of such counterparts to the Issuers.

                              Very truly yours,

                              TRIDEX CORPORATION

                              By /s/ George T. Crandall, V.P. & Treasurer
                                 ----------------------------------------
                                                            (Title)

                              PROGRESSIVE SOFTWARE, INC.

                              By /s/ George T. Crandall, V.P. & Treasurer
                                 ----------------------------------------
                                                            (Title)

                              ULTIMATE TECHNOLOGY CORPORATION

                              By /s/ George T. Crandall, V.P. & Treasurer
                                 ----------------------------------------
                                                            (Title)

The foregoing is hereby accepted and agreed to.

MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY

By:  David L. Babson and Company Incorporated, its Investment Adviser

By /s/ Clifford M. Noreem
   ------------------------
                  (Title)

<PAGE>

MASSMUTUAL CORPORATE INVESTORS

By /s/ Clifford M. Noreem
   ------------------------
                  (Title)

The foregoing is executed on behalf of
MassMutual Corporate Investors,
organized under a Declaration of Trust,
dated September 13, 1985, as amended
from time to time. The obligations of
such Trust are not personally binding
upon, nor shall resort be had to the
property of, any of the Trustees,
shareholders, officers, employees, or
agents of such Trust, but the Trust's
property only shall be bound.

MASSMUTUAL PARTICIPATION INVESTORS

By /s/ Clifford M. Noreem
   ------------------------
                  (Title)

The foregoing is executed on behalf of
MassMutual Participation Investors,
organized under a Declaration of Trust,
dated April 7, 1988, as amended from
time to time. The obligations of such
Trust are not personally binding upon,
nor shall resort be had to the property
of, any of the Trustees, shareholders,
officers, employees, or agents of such
Trust, but the Trust's property only
shall be bound.

MASSMUTUAL CORPORATE VALUE PARTNERS LIMITED

By:   David L. Babson and Company Incorporated, under delegated authority from
      Massachusetts Mutual Life Insurance Company, its Investment Manager

By /s/ Clifford M. Noreem
   ------------------------
                  (Title)

 The foregoing is hereby acknowledged and assented to:

FLEET NATIONAL BANK

By /s/ Vincent J. Pitts
   ------------------------
                  (Title)

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