Document:

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                               FIRST AMENDMENT TO
                               ------------------

              AMENDED AND RESTATED SENIOR SECUREDLOAN AND SECURITY
              ----------------------------------------------------

                                    AGREEMENT
                                    ---------

          THIS FIRST AMENDMENT TO AMENDED AND RESTATED SENIOR SECURED LOAN AND
SECURITY AGREEMENT (the "Amendment") is made as of September 25, 2001 between
Landmark Communications, Inc. (hereinafter, "Lender"), a corporation organized
and existing under the laws of the Commonwealth of Virginia having an office at
150 W. Brambleton Avenue, Norfolk, Virginia 23510, and CoolSavings, Inc.
(hereinafter, "Borrower"), a Delaware corporation with its principal executive
offices at 360 N. Michigan Ave., 19/th/ Floor, Chicago, Illinois 60601, that is
the successor in interest to coolsavings.com inc., a Michigan corporation
("Predecessor"), in consideration of the mutual covenants contained herein and
benefits to be derived herefrom. All capitalized terms shall have the meaning
ascribed to them in the Amended and Restated Senior Secured Loan and Security
Agreement dated July 30, 2001 (the "Loan and Security Agreement").

                              W I T N E S S E T H:
                              -------------------

          WHEREAS, Predecessor entered into the Loan and Security Agreement
pursuant to which Borrower, among other things, agreed to repay on demand any
Advances (as defined in the Loan and Security Agreement) that Lender in its sole
discretion agreed to make under the Grid Note (as defined in the Loan and
Security Agreement), provided such Advances were not to exceed in the aggregate
$5,000,000 (the "Maximum Principal Amount"); and

          WHEREAS, the parties hereto desire to amend Section 1.1(b) of the Loan
and Security Agreement principally to increase the amount of the Maximum
Principal Amount.

          NOW THEREFORE, in consideration of the above recitals and for other
good and valuable consideration, the receipt and adequacy of which are hereby
acknowledged, the parties hereto agree as follows:

          SECTION 1. Amendment.
                     ---------

          Section 1.1(b) of the Loan and Security Agreement is hereby amended
                                                                      -------
and restated in its entirety as follows:
    --------

                1.1(b) For value received Borrower unconditionally promises to
          pay to the order of Lender ON DEMAND, without offset, the unpaid
          principal amount of any and all sums advanced to the Borrower, at the
          Lender's sole discretion, from time to time (an "Advance") and
                                                           -------
          outstanding under that certain Commercial Demand Grid Note attached
          hereto as Exhibit C, as the same may be amended, restated,
                    ---------
          supplemented or otherwise modified from time to time (the "Grid
                                                                     ----
          Note"), together with interest on each and all such Advances from the
          ----
          date of any such Advance which shall accrue and compound thereon at
          the interest rates set forth below (the Initial Loan together with any

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          and all Advances, the "Loan"). Notwithstanding the foregoing, the
                                 ----
          aggregate amount of any Advances under the Grid Note shall at no time
          exceed Twenty Million Dollars ($20,000,000). Lender shall not be
          obligated to make any Advance to Borrower at any time and should
          Lender, in its sole discretion, make an Advance, the decision to
          evidence Borrower's repayment obligation with respect thereto under
          the Grid Note shall also be at Lender's sole discretion. The Grid Note
          shall be a demand obligation which shall be payable by the Borrower at
          Lender's demand at any time and from time to time. For purposes of
          this Agreement, "Advance" shall be deemed to include any reimbursement
          obligation of Borrower to Lender that Lender records as an advance
          under the Grid Note.

          SECTION 2. Survival. Except as expressly amended hereby, the Loan and
                     --------
Security Agreement and all other provisions contained therein except those
specifically amended hereby shall continue in full force and effect in
accordance with the provisions thereof and the Loan and Security Agreement is in
all respects hereby ratified, confirmed and preserved. This Amendment and all
its provisions shall be deemed a part of the Loan and Security Agreement in the
manner and to the extent herein provided.

          SECTION 3. Successors and Assigns. This Amendment shall be binding
                     ----------------------
upon and inure to the benefit of the parties hereto and their respective
successors and permitted assigns.

          SECTION 4. Governing Law. This Amendment shall be governed by Illinois
                     -------------
law without reference to its choice of law doctrine.

          SECTION 5. Counterparts. This Amendment may be executed in any number
                     ------------
of counterparts, all of which taken together shall constitute one and the same
instrument, and any of the parties hereto may execute this Amendment by signing
any such counterpart.

          IN WITNESS WHEREOF, the parties hereto have caused this Amendment to
be duly executed as of the date first written above.

                           Borrower:
                           CoolSavings, Inc.

                           By:    /s/ Matthew Moog
                              --------------------------------------------------
                           Print Name: Matthew Moog
                                      ------------------------------------------
                           Title:       Chief Executive Officer
                                 -----------------------------------------------

                           Lender:
                           Landmark Communications, Inc.

                           By:  /s/ Guy R. Friddell. III
                              --------------------------------------------------
                           Print Name: Guy R. Friddell. III
                                      ------------------------------------------
                           Title: Executive Vice President
                                 -----------------------------------------------

                                        2<PAGE>

                AMENDED AND RESTATED COMMERCIAL DEMAND GRID NOTE

$ ______________                                            September 28, 2001
(Up to $20 million)                                         Chicago, Illinois

                                    RECITALS:
                                    --------

     A. coolsavings.com inc., a Michigan corporation ("Predecessor") made a
                                                       -----------
Commercial Demand Grid Note dated July 30, 2001 (the "Initial Note") in favor of
                                                      ------------
Landmark Communications, Inc., a Virginia corporation ("Lender") to evidence
                                                        ------
Predecessor's obligation to repay Lender for up to $5,000,000 advanced to the
Initial Note.

     B. As a result of advances on August 14, 2001 and September 25, 2001 under
the Initial Note, the principal amount outstanding under the Initial Note is
$5,000,000 (the "Existing Principal Amount Outstanding").
                 -------------------------------------

     C. Predecessor has merged with and into CoolSavings, Inc., a Delaware
corporation ("Borrower"), and Borrower has assumed all of Predecessor's debts,
              --------
obligations and liabilities under the Initial Note.

     D. Borrower desires to amend and restate the Initial Note to increase the
maximum principal amount thereunder to $20,000,000, and Lender is willing to
accept such amendment and restatement, on the terms and conditions set forth
herein.

     NOW, THEREFORE, for value received, Borrower unconditionally promises to
pay ON DEMAND to the order of Lender, without offset, at 150 W. Brambleton
Avenue, Norfolk, VA 23510, or at such other place as the holder of this Amended
and Restated Commercial Demand Grid Note ("Note") may designate from time to
                                           ----
time in writing, the unpaid principal amount of all sums advanced and
outstanding hereunder, including, without limitation, the Existing Principal
Amount Outstanding (the "Principal Amount Outstanding"), as set forth on the
                         ----------------------------
attached Schedule of Advances and Payments of Principal (the "Schedule"),
                                                              --------
together with interest on the Principal Amount Outstanding from the date of each
advance at the rate, and on the terms and conditions, set forth below. (For the
avoidance of doubt, interest on the Existing Principal Amount Outstanding shall
accrue from the applicable dates that the Advances (defined below) included
within such sum were advanced notwithstanding the date of this Note.) Each
"Advance", as defined in that certain Amended and Restated Loan and Security
 -------
Agreement dated July 30, 2001, as amended from time to time, between Borrower
and Lender (the "Loan Agreement"), shall, at Lender's option, be an installment
                 --------------
of principal advanced hereunder. Lender shall be under no obligation to make
advances hereunder or under the Loan Agreement. Capitalized terms not otherwise
defined herein shall have the meaning given such terms under the Loan Agreement.
All obligations under this Note shall be pari passu with the Senior Secured
Note, consistent with the Loan Agreement.

        1. Demand Right; Payment of Note. Lender may demand at any time and from
           -----------------------------
time to time in whole or in part the payment of the Principal Amount Outstanding
and all accrued and unpaid interest on this Note.

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        2.  Interest; Default Rate.
            ----------------------

        (a) The Principal Amount Outstanding shall bear interest at the rate of
eight percent (8%) per annum. Interest shall be computed on the actual number of
days elapsed on the basis of a year consisting of 360 days.

        (b) Any amounts outstanding under this Note that shall have been
demanded by the Lender hereto and not paid shall bear interest from and after
the date of such applicable demand at the rate of sixteen (16%) per annum (the
"Demand Interest Rate"), increasing monthly by an annual rate which is one (1)
 --------------------
percentage point above the then current Demand Interest Rate for each month that
any amounts outstanding under this Note remain overdue. Any interest on the Note
shall accrue and be compounded monthly until the obligation of Borrower, with
respect to the payment of such interest, has been discharged (whether before or
after judgment).

        (c) Notwithstanding the foregoing, the effective annual rate under this
Note (including the Demand Interest Rate) shall not exceed a maximum annual rate
of twenty-four (24%) percent or the maximum annual rate permitted by law,
whichever is less.

        3.  Prepayment. Borrower may prepay the Principal Amount Outstanding and
            ----------
all accrued interest under this Note at any time and from time to time;
provided, such prepayment shall not cause a breach or event of default under
Borrower's agreements with American National Bank and Trust Company of Chicago
or be permitted at any time that Borrower has failed to declare and pay all
dividends required to be declared and paid under Borrower's certificate of
incorporation; and, provided, further, that payment of any outstanding principal
or interest (whether a prepayment or in response to a demand) shall not
extinguish or terminate this Note as it shall secure Borrower's obligations to
pay Advances under the Loan Agreement until the Loan Agreement has been
terminated.

        4.  Application of Payments. All payments made on this Note may be
            -----------------------
applied, at the option of Lender, first in payment of any costs or expenses of
Lender due hereunder, then in payment of any late charges due hereunder, then in
payment of any accrued and unpaid interest due hereunder, and any balance shall
be applied in payment of the Principal Amount Outstanding under this Note. At
Lender's sole discretion, Lender may forgive any portion of any principal or
interest amounts due under this Note and unpaid as effective payment of any
portion of the exercise price of any warrants to purchase common stock of the
Borrower that Lender then holds and wishes to exercise. Each payment tendered to
Lender on this Note shall be payable in lawful money of the United States which
shall be legal tender for public and private debts at the time of payment. Any
check given in payment of any amounts due hereunder will constitute a payment
only when collected. In the event Lender shall incur any cost or expense or make
any advance or other disbursement under the terms and conditions of any document
or instrument relating to the indebtedness of Borrower to Lender evidenced by
this Note or any document or instrument providing Lender with any security for
the payment of this Note, then, any payment made to Lender under this Note may
be applied, at the option of Lender, first to the payment of any such cost,
expense, advance or disbursement and all interest due thereon, and the balance,
if any, of such payment applied as aforesaid towards the payment of any amounts
then due and payable under this Note.

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        5.  Waivers. Borrower waives presentment, demand, protest, notice of
            -------
dishonor and all other notices of every kind and nature to which Borrower would
otherwise be entitled under the applicable law. Borrower agrees that Lender may
take any one or more of the following actions, on one or more occasions, whether
before or after the maturity of this Note, without any notice to Borrower,
without any further consent to such actions, and without releasing or
discharging Borrower from liability on the Note:

        (a) Any extension or extensions of the time of payment of any principal,
interest or other amount due and payable under this Note;

        (b) Any renewal of this Note, in whole or in part;

        (c) Any full or partial release or discharge from liability under this
Note of any other Borrower;

        (d) Any release, in whole or in part, of any security for the payment of
all or any portion of the amounts due under this Note;

        (e) Any waiver of any default under any Loan Document;

        (f) Any failure or refusal of Lender to (i) realize on any security
which Lender may have for the payment of this Note, (ii) institute any suit or
action against Borrower under this Note, (iii) exercise any other right or
remedy available to Lender under this Note or applicable law, or any delay by
Lender in realizing on any such security, in instituting any such suit or
action, or in exercising any other such right or remedy;

        (g) Any agreement with Borrower changing the rate of interest or any
other term or condition of this Note; or

        (h) Any failure or refusal of Lender to obtain or maintain a valid,
perfected and enforceable lien against any real and/or personal property
securing the payment of this Note, in whole or in part.

     To the fullest extent permitted by law, Borrower waives the benefit of all
laws and rules of law intended for his protection or advantage as a party liable
on this Note or providing for its release or discharge from liability upon the
failure or refusal of Lender to perform certain acts, including, but not limited
to, the realization by Lender on any security for the payment of this Note and
any law and any rule of law requiring Lender to institute any suit or action on
this Note, but excluding any statute of limitations applicable to the collection
or enforcement of this Note.

        6.  Security. This Note is secured as provided in the Loan Agreement.
            --------

        7.  Completion of Schedule. It is understood and agreed that any officer
            ----------------------
or authorized employee of Lender may make entries on the Schedule (and on any
supplemental schedules attached hereto) (i) upon receipt of written or
telephonic instructions of any one reasonably believed by such officer or
authorized employees to be an authorized agent of Borrower or (ii) when an
Advance is made pursuant to the Loan Agreement. Borrower shall

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indemnify and hold Lender harmless from and against any and all claims, damages,
losses, costs and expenses (including attorneys' fees) which may arise or be
created by the acceptance of instructions for making or paying advances by
telephone. The Principal Amount Outstanding shown on the Schedule shall be prima
facie evidence of the principal amount owing and unpaid on this Note. The
failure to record the date an amount of any advance on the Schedule shall not,
however, limit or otherwise affect the obligations of Borrower under this Note
to repay the principal amount of the advance together with all interested
accruing thereon.

        8.  Events of Default. Any Event of Default under the Loan Agreement
            -----------------
shall constitute an event of default under this Note.

        9.  Acceleration; Remedies. Upon an event of default, the entire
            ----------------------
Principal Amount Outstanding, and all accrued and unpaid interest, and all other
sums required under this Note and the Loan Agreement shall, notwithstanding the
stated maturity in this Note, become immediately due and payable, without notice
or demand to Borrower. Upon default, Lender shall have the right, immediately
and without notice to Borrower or the taking of any other action, to set-off
against this Note, all liabilities of Lender to Borrower and all obligations for
money or money's worth owed by Lender to Borrower, whether or not due, without
notice to Borrower (such liabilities and obligations including, without
limitation, all money, stocks, bonds or other security or property of any kind
or nature held by or in the possession of Lender to or for the credit of
Borrower); and Lender shall be deemed to have made a charge against any such
liabilities or obligations immediately upon the occurrence of any event of
default under this Note even though such charge is subsequently made or entered
on the behalf of Lender. The remedies provided in this Note upon default and in
other agreement between Lender and Borrower are cumulative and not exclusive of
any other remedies provided under the Loan Agreement or at law or in equity.

        10. Additional Provisions.
            ---------------------

        (a) To the extent permitted by generally accepted accounting principles,
Borrower will treat, account and report the Note as debt and not equity for
accounting purposes and with respect to any returns filed with federal, state or
local tax authorities.

        (b) No delay or omission by Lender in exercising or enforcing any of
Lender's powers, rights, privileges, remedies, or discretions hereunder shall
operate as a waiver thereof on that occasion nor on any other occasion. No
waiver of any default hereunder shall operate as a waiver of any other default
hereunder, nor as a continuing waiver.

        (c) Borrower, and each endorser and guarantor, if any, of this Note,
shall indemnify, defend, and hold Lender harmless against any claim brought or
threatened against Lender by Borrower (other than a claim which is finally
judicially determined against Lender), by any endorser or guarantor, or by any
other person (as well as from attorneys' reasonable fees and expenses in
connection therewith) on account of Lender's relationship with Borrower or any
endorser or guarantor hereof (each of which may be defended, compromised,
settled or pursued by Lender with counsel of Lender's selection, but at the
expense of Borrower and any endorser and/or guarantor).

                                        4

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          (d) Borrower will pay on demand all attorneys' reasonable fees and
out-of-pocket expenses incurred by Lender in the administration of all
Liabilities and obligations of Borrower to Lender, including, without
limitation, costs and expenses associated with travel on behalf of Lender.
Borrower will also pay on demand, without limitation, all attorneys' reasonable
fees, out-of-pocket expenses incurred by Lender's attorneys and all costs
incurred by Lender, including, without limitation, costs and expenses associated
with travel on behalf of Lender, which costs and expenses are directly or
indirectly related to the protection or enforcement of any of Lender's rights
against Borrower or any such endorser or guarantor and against any collateral
given Lender to secure this Note or any other Liabilities of Borrower or such
endorser and guarantor to Lender (whether or not suit is instituted by or
against Lender).

          (e) Borrower, and each endorser and guarantor of this Note,
respectively waives presentment, demand, notice, and protest, and also waives
any delay on the part of the holder hereof. Each assents to any extension or
other indulgence (including, without limitation, the release or substitution of
collateral) permitted Borrower or any endorser or guarantor by Lender with
respect to this Note and/or any collateral given to secure this note or any
extension or other indulgence, as described above, with respect to any other
liability or any collateral given to secure any other liability of Borrower or
any endorser or guarantor to Lender.

          (f) This Note shall be binding upon Borrower and each endorser and
guarantor hereof and upon their respective heirs, successors, assigns, and
representatives, and shall inure to the benefit of Lender and its successors,
endorsees, and assigns.

          (g) The liabilities of Borrower and any endorser or guarantor of this
Note are joint and several; provided, however, that the release by Lender of
Borrower or any one or more endorser or guarantor shall not release any other
person obligated on account of this Note. Each reference in this Note to
Borrower, any endorser, and any guarantor, is to such person individually and
also to all such persons jointly. No person obligated on account of this Note
may seek contribution from any other person also obligated unless and until all
liabilities, obligations and indebtedness to Lender of the person from whom
contribution is sought have been satisfied in full.

          (h) Borrower and each endorser and guarantor hereof each authorizes
Lender to complete this Note if delivered incomplete in any respect.

          (i) This Note is delivered to Lender at its offices at 150 W.
Brambleton Avenue, Norfolk, VA 23510, shall be governed by the laws of the State
of Illinois, and shall take effect as a sealed instrument. Borrower and each
endorser and guarantor of this Note each submits to the jurisdiction of the
courts of the State of Illinois for all purposes with respect to this Note, any
collateral given to secure their respective liabilities, obligations and
indebtedness to Lender, and their respective relationships with Lender. Any
determination that any provision of this Note or any application thereof is
invalid, illegal or unenforceable in any respect in any instance shall not
affect the validity, legality or enforceability of such provision in any other
instance, or the validity, legality or enforceability of any other provision of
this Note.

          (j) The undersigned makes the following waiver knowingly, voluntarily,
and intentionally, and understands that Lender, in the establishment and
maintenance of Lender's

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relationship with Borrower contemplated by the within Note, is relying thereon.
THE UNDERSIGNED, TO THE EXTENT ENTITLED THERETO, WAIVES ANY PRESENT OR FUTURE
                                                 ------
RIGHT OF THE UNDERSIGNED, OR OF ANY GUARANTOR OR ENDORSER OF THE UNDERSIGNED OR
OF ANY OTHER PERSON LIABLE TO LENDER ON ACCOUNT OF OR IN RESPECT TO THE
LIABILITIES, TO A TRIAL BY JURY IN ANY CASE OR CONTROVERSY IN WHICH LENDER IS OR
BECOMES A PARTY (WHETHER SUCH CASE OR CONTROVERSY IS INITIATED BY OR AGAINST
LENDER OR IN WHICH LENDER IS JOINED AS A PARTY LITIGANT), WHICH CASE OR
CONTROVERSY ARISES OUT OF, OR IS IN RESPECT TO, ANY RELATIONSHIP AMONGST OR
BETWEEN THE UNDERSIGNED, ANY SUCH PERSON, AND LENDER.

          (k) Borrower has read all of the terms and conditions of this Note and
acknowledges receipt of an exact copy of it.

                  [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK -
                             SIGNATURE PAGE FOLLOWS]

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         WITNESS the following signature(s) and seal(s):

                                    COOLSAVINGS, INC.

                                    By:    /s/ Matthew Moog
                                       ---------------------------------------

                                    Print Name: Matthew Moog
                                               -------------------------------

                                    Title:        Chief Executive Officer
                                          ------------------------------------

ATTEST:

       /s/ Joyce Evans
---------------------------------
Name:  Joyce Evans
     ----------------------------
Title: Executive Assistant
      ---------------------------

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                 SCHEDULE OF ADVANCES AND PAYMENTS OF PRINCIPAL

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                                                  Principal        Approving
                                                    Amount         Initials
        Date            Advance      Payment     Outstanding       Initials

-------------------------------------------------------------------------------
   August 14, 2001     $2,500,000                $2,500,000
-------------------------------------------------------------------------------
 September 25, 2001    $2,500,000                $5,000,000
-------------------------------------------------------------------------------
 September 28, 2001    $2,500,000                $7,500,000
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