SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                  SCHEDULE 13D

             INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT
            TO RULE 13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO
                                  RULE 13d-2(a)

                           (Amendment No. _________)*


                                Insure.com, Inc.
             -------------------------------------------------------
                                (Name of Issuer)


                     Common Stock, par value $.003 per share
             -------------------------------------------------------
                         (Title of Class of Securities)


                                    45807N109
               --------------------------------------------------
                                 (CUSIP Number)


                              Osmium Partners, LLC
                          388 Market Street, Suite 920
                             San Francisco, CA 94111
                            Attention: John H. Lewis
                            Telephone: (415) 362-4485
             -------------------------------------------------------
                  (Name, Address and Telephone Number of Person
                Authorized to Receive Notices and Communications)


                                  May 30, 2008
             -------------------------------------------------------
             (Date of Event Which Requires Filing of this Statement)


         If the filing person has previously filed a statement on Schedule 13G
to report the acquisition that is the subject of this Schedule 13D, and is
filing this schedule because of Rule 13d-1(e), 13d-1(f) or 13d-1(g), check the
following box [X].

         Note. Schedules filed in paper format shall include a signed original
and five copies of the schedule, including all exhibits. See Rule 13d-7(b) for
other parties to whom copies are to be sent.

* The remainder of this cover page shall be filled out for a reporting person's
initial filing on this form with respect to the subject class of securities, and
for any subsequent amendment containing information which would alter
disclosures provided in a prior cover page.

The information required on the remainder of this cover page shall not be deemed
to be "filed" for the purpose of Section 18 of the Securities Exchange Act of
1934 or otherwise subject to the liabilities of that section of the Act but
shall be subject to all other provisions of the Act (however, see the Notes.)

                               Page 1 of 10 pages


CUSIP No.:  45807N109

1.   NAME OF REPORTING PERSON
     S.S. OR I.R.S. IDENTIFICATION NO. OF ABOVE PERSON

     John H. Lewis

2    CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
     (a) [ ]
     (b) [X]

3    SEC USE ONLY

4    SOURCE OF FUNDS

     PF

5    CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM
     2(d) or 2(e) [ ]

6.   CITIZENSHIP OR PLACE OF ORGANIZATION

     United States

NUMBER OF                        7        SOLE VOTING POWER   -  500
SHARES
BENEFICIALLY                     8        SHARED VOTING POWER   -  423,112
OWNED BY
EACH                             9        SOLE DISPOSITIVE POWER   -  500
REPORTING
PERSON WITH                      10       SHARED DISPOSITIVE POWER  -  423,112

11   AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON

     423,612

12   CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES [ ]

13   PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)

     6.0%

14   TYPE OF REPORTING PERSON

     IN

                               Page 2 of 10 pages


CUSIP No.:  45807N109

1    NAME OF REPORTING PERSON
     S.S. OR I.R.S. IDENTIFICATION NO. OF ABOVE PERSON

     Osmium Partners, LLC

2    CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
     (a) [ ]
     (b) [X]

3    SEC USE ONLY

4    SOURCE OF FUNDS

     AF

5    CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM
     2(d) or 2(e) [ ]

6    CITIZENSHIP OR PLACE OF ORGANIZATION

     Delaware

NUMBER OF                        7        SOLE VOTING POWER   -  0
SHARES
BENEFICIALLY                     8        SHARED VOTING POWER   -  423,112
OWNED BY
EACH                             9        SOLE DISPOSITIVE POWER  -  0
REPORTING
PERSON WITH                      10       SHARED DISPOSITIVE POWER  -  423,112

11   AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON

     423,112

12   CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES [ ]

13   PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)

     6.0%

14   TYPE OF REPORTING PERSON

     OO

                               Page 3 of 10 pages


CUSIP No.:  45807N109

1    NAME OF REPORTING PERSON
     S.S. OR I.R.S. IDENTIFICATION NO. OF ABOVE PERSON

     Osmium Capital, LP

2    CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
     (a) [ ]
     (b) [X]

3    SEC USE ONLY

     SOURCE OF FUNDS

     WC

5    CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM
     2(d) or 2(e) [ ]

6    CITIZENSHIP OR PLACE OF ORGANIZATION

     Delaware

NUMBER OF                        7        SOLE VOTING POWER   -  0
SHARES
BENEFICIALLY                     8        SHARED VOTING POWER   -  136,376
OWNED BY
EACH                             9        SOLE DISPOSITIVE POWER   -  0
REPORTING
PERSON WITH                      10       SHARED DISPOSITIVE POWER  -  136,376

11   AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON

     136,376

12   CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES [ ]

13   PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)

     1.9%

14   TYPE OF REPORTING PERSON

     PN

                               Page 4 of 10 pages


CUSIP No.:  45807N109

1    NAME OF REPORTING PERSON
     S.S. OR I.R.S. IDENTIFICATION NO. OF ABOVE PERSON

     Osmium Capital II, LP

2    CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
     (a) [ ]
     (b) [X]

3    SEC USE ONLY

4    SOURCE OF FUNDS

     WC

5    CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM
     2(d) or 2(e) [ ]

6    CITIZENSHIP OR PLACE OF ORGANIZATION

     Delaware

NUMBER OF                        7        SOLE VOTING POWER   -  0
SHARES
BENEFICIALLY                     8        SHARED VOTING POWER   -  204,768
OWNED BY
EACH                             9        SOLE DISPOSITIVE POWER   -  0
REPORTING
PERSON WITH                      10       SHARED DISPOSITIVE POWER  -  204,768

11   AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON

     204,768

12   CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES [ ]

13   PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)

     2.9%

14   TYPE OF REPORTING PERSON

     PN

                               Page 5 of 10 pages


CUSIP No.:  45807N109

1    NAME OF REPORTING PERSON
     S.S. OR I.R.S. IDENTIFICATION NO. OF ABOVE PERSON

     Osmium Spartan, LP

2    CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
     (a) [ ]
     (b) [X]

3    SEC USE ONLY

4    SOURCE OF FUNDS

     WC

5    CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM
     2(d) or 2(e) [ ]

6    CITIZENSHIP OR PLACE OF ORGANIZATION

     Delaware

NUMBER OF                        7        SOLE VOTING POWER   -  0
SHARES
BENEFICIALLY                     8        SHARED VOTING POWER   -  81,968
OWNED BY
EACH                             9        SOLE DISPOSITIVE POWER   -  0
REPORTING
PERSON WITH                      10       SHARED DISPOSITIVE POWER  -  81,968

11   AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON

     81,968

12   CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES [ ]

13   PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)

     1.2%

14   TYPE OF REPORTING PERSON

     PN

                               Page 6 of 10 pages


ITEM 1.  Security and Issuer.

         The class of equity securities to which this Statement on Schedule 13D
(this "Statement") relates is the common stock, par value $0.003 per share (the
"Common Stock"), of Insure.com, Inc. (the "Issuer"), with its principal
executive offices located at 8205 South Cass Avenue, Suite 102, Darien, Illinois
60561.

ITEM 2.  Identity and Background.

         (a)-(c) and (f) The names of the persons filing this statement on
Schedule 13D (the "Reporting Persons") are:

         -Osmium Capital, LP, a Delaware limited partnership ("Fund I");

         -Osmium Capital II, LP, a Delaware limited partnership ("Fund II");

         -Osmium Spartan, LP, a Delaware limited partnership ("Fund III");

         -Osmium Partners, LLC, a Delaware limited liability company ("Osmium
Partners"); and

         -John H. Lewis, a United States Citizen ("Lewis").

         Osmium Partners serves as the general partner of Fund I, Fund II and
Fund III. Mr. Lewis is the managing member of Osmium Partners.

         Osmium Partners and Mr. Lewis may each be deemed to have voting and
dispositive power with respect to the shares of Common Stock held by Fund I,
Fund II and Fund III.

         The principal business of each of Fund I, Fund II and Fund III is that
of a private investment vehicle engaged in investing and trading in a wide
variety of securities and financial instruments for its own account.

         The principal business of Osmium Partners is providing investment
management services and serving as the general partner of Fund I, Fund II and
Fund III. Osmium Partners also manages other accounts on a discretionary basis.

         Mr. Lewis' principal occupation is serving as the managing member of
Osmium Partners.

         (d)-(e) During the last five years, none of the Reporting Persons have
been (a) convicted in a criminal proceeding (excluding traffic violations or
similar misdemeanors) or (b) a party to a civil proceeding of a judicial or
administrative body of competent jurisdiction and as a result of such proceeding
was or is subject to a judgment, decree or final order enjoining future
violations of, or prohibiting or mandating activities subject to, federal or
state securities laws or finding any violation with respect to such laws.

ITEM 3.  Source and Amount of Funds or Other Consideration

         The source and amount of funds (excluding commissions) used by the
Funds in making their purchase of the shares of Common Stock owned by each of
them in aggregate was $1,713,604 from working capital.

         The source and amount of funds (excluding commissions) used by Mr.
Lewis in making his purchase of the shares of Common Stock owned by him was
$2,075 from personal funds.

         One or more of the Reporting Persons effect purchases of securities
through margin accounts which may extend margin credit to the Reporting Persons
as and when required to open or carry positions in the margin accounts, subject
to applicable federal margin regulations, stock exchange rules and brokers'
credit policies. In such instances, the positions held in the margin accounts
are pledged as collateral security for the repayment of debit balances in the
accounts.

                               Page 7 of 10 pages


ITEM 4.  Purpose of Transaction.

         On May 30, 2008, Osmium Partners sent a letter to the Board of
Directors of the Issuer, which, among other things, expresses disappointment
with the performance of the Issuer and recommends that the Issuer engage a
banker and immediately progress with a sale of the Issuer. A copy of the letter
from Osmium Partners is attached hereto as Exhibit B.

         All of the shares of Common Stock reported herein as being beneficially
owned by the Reporting Persons were acquired for investment purposes. Except as
set forth herein, none of the Reporting Persons has any plans or proposals that
relate to or would result in any of the transactions described in subparagraphs
(a) through (j) of Item 4 of Schedule 13D.

         Also, consistent with their investment purpose, the Reporting Persons
may engage in communications with one or more shareholders of the Issuer, one or
more officers or employees of the Issuer, one or more members of the board of
directors of the Issuer, and/or one or more representatives of the Issuer
regarding the Issuer, including but not limited to its management, operations,
business, results, plans, and prospects. The Reporting Persons may discuss ideas
that, if effected, may result in any of the following: the acquisition by
persons of additional Common Stock or other securities of the Issuer, an
extraordinary corporate transaction involving the Issuer, and/or changes in the
board of directors or management of the Issuer.

ITEM 5.  Interest in Securities of the Issuer.

         (a)      The Reporting Persons beneficially own:

                  (i)      Fund I directly owns 136,376 shares of Common Stock
                           representing 1.9% of all of the outstanding shares of
                           Common Stock.

                  (ii)     Fund II directly owns 204,768 shares of Common Stock
                           representing 2.9% of all of the outstanding shares of
                           Common Stock.

                  (iii)    Fund III directly owns 81,968 shares of Common Stock
                           representing 1.2% of all of the outstanding shares of
                           Common Stock.

                  (iv)     Mr. Lewis directly owns 500 shares of Common Stock
                           representing 0.007% of all of the outstanding shares
                           of Common Stock.

                  (v)      Osmium Partners, as the general partner of Fund I,
                           Fund II and Fund III, may be deemed to beneficially
                           own the 423,112 shares of Common Stock held by them,
                           representing 6.0% of all of the outstanding shares of
                           Common Stock.

                  (vi)     Mr. Lewis may be deemed to be the beneficial owner of
                           the shares of Common Stock beneficially owned by
                           Osmium Partners.

                  (vii)    Collectively, the Reporting Persons beneficially own
                           423,612 shares of Common Stock representing 6.0% of
                           all of the outstanding shares of Common Stock.

                  Each Reporting Person disclaims beneficial ownership with
                  respect to any shares of Common Stock other than the shares
                  owned directly and of record by such Reporting Person.

                  The percentages set forth in this response are based on the
                  7,068,160 shares of Common Stock outstanding as of May 2,
                  2008, as reported by the Issuer in its Quarterly Report on
                  Form 10-Q for the quarterly period ended March 31, 2008.

         (b)      Osmium Partners, Fund I and Mr. Lewis have shared power to
vote or direct the vote of and to dispose or direct the disposition of the
136,376 shares of Common Stock held by Fund I.

                               Page 8 of 10 pages


         Osmium Partners, Fund II and Mr. Lewis have shared power to vote or
direct the vote of and to dispose or direct the disposition of the 204,768
shares of Common Stock held by Fund II.

         Osmium Partners, Fund III and Mr. Lewis have shared power to vote or
direct the vote of and to dispose or direct the disposition of the 81,968 shares
of Common Stock held by Fund III.

         Mr. Lewis has sole power to vote or direct the vote of and to dispose
or direct the disposition of the 500 shares of Common Stock held by him.

         (c)      The Funds engaged in the following transactions on the open
market with respect to the Issuer's Common Stock:

         Transaction       Number of        Price             Type of
         Date              Shares           per Share         Transaction
         ----------------------------------------------------------------
         3/28/08           100              $3.7588           Purchase
         3/31/08           300              $3.87             Purchase
         4/14/08           6,400            $3.80             Purchase
         4/14/08           6,400            $3.80             Sale

         Other than the foregoing, no transactions in the Common Stock have been
effected by the Reporting Persons in the last sixty (60) days.

         (d)      Not applicable.

         (e)      Not applicable.

ITEM 6.  Contracts, Arrangements, Understandings or Relationships With Respect
         to Securities of the Issuer.

         Not applicable.

ITEM 7.  Material to be Filed as Exhibits.

         Exhibit A - Joint Filing Agreement

         Exhibit B - Letter to Board of Directors of Issuer


                               Page 9 of 10 pages


                                   SIGNATURE

         After reasonable inquiry and to the best of its knowledge and belief,
the undersigned each certifies that the information with respect to it set forth
in this Statement is true, complete and correct.

Dated:  June 2, 2008

        John H. Lewis
        Osmium Partners, LLC
        Osmium Capital, LP
        Osmium Capital II, LP
        Osmium Spartan, LP

        By: /s/ JOHN H. LEWIS
            ---------------------------------------
            John H. Lewis, for himself and as
            Managing Member of Osmium Partners, LLC




                               Page 10 of 10 pages


                                  EXHIBIT INDEX


Exhibit A - Joint Filing Agreement

Exhibit B - Letter to Board of Directors of Issuer




                                    EXHIBIT A

                             JOINT FILING AGREEMENT

         The undersigned hereby agree that the statement on Schedule 13D with
respect to the Common Stock, par value $0.003 per share, of Insure.com, Inc.
dated as of June 2, 2008 is, and any amendments thereto signed by each of the
undersigned shall be, filed pursuant to and in accordance with the provisions of
Rule 13(d)-1(k) under the Securities Exchange Act of 1934, as amended.

Dated:  June 2, 2008


        John H. Lewis
        Osmium Partners, LLC
        Osmium Capital, LP
        Osmium Capital II, LP
        Osmium Spartan, LP

        By: /s/ JOHN H. LEWIS
            ---------------------------------------
            John H. Lewis, for himself and as
            Managing Member of Osmium Partners, LLC