EXHIBIT 10.10


June 19, 2002

Wisconsin United For Health Foundation, Inc.
c/o Charles Henderson
Davis & Kuelthau, S.C.
111 East Kilbourn Avenue, Suite 1400
Milwaukee, WI 53202

Ladies and Gentlemen:

         We are writing to confirm our understanding concerning a proposed
public offering of common stock, no par value, of Cobalt Corporation (the
"Company").

         We have jointly begun the process of preparing to sell, in a single
underwritten public offering, a total of 7.5 million shares of Company stock,
consisting of 5.0 million outstanding shares owned beneficially by yourselves
(the "Foundation") and 2.5 million shares to be newly issued by the Company.
These shares are referred to herein as the "Firm Shares." It is understood that
these numbers at this time are subject to (i) further consideration by the
Foundation's Board of Directors, (ii) the exercise or non-exercise by the
underwriters of the customary over-allotment option, and (iii) increase or
reduction in the number of shares finally offered based upon recommendations by
the underwriters. However, the Board of Directors of the Company has authorized
the sale of no more than 3 million newly issued shares in total, and the number
of shares offered by the Company will in no event exceed the number of shares
offered by the Foundation.

         In connection with the proposed offering, we have agreed as follows:

         1. The registration of shares in the offering on behalf of the
Foundation ("Registration") will not be deemed a Demand Registration for
purposes of Section 2(d)(i) or 2(d)(ii) of the Registration Rights Agreement
between us dated as of March 23, 2001.

         2. Any exercise of the underwriters' over-allotment option will be
satisfied in its entirety by shares offered by the Foundation.

         3. In the event the underwriters indicate an ability to sell a greater
number of shares than the number initially registered, the Foundation will have
the first right (but not the obligation) to provide such shares.

         4. In the event the underwriters determine that marketing or other
factors require a limitation on the number of shares to be offered, the
Foundation will allow its allotment of Firm Shares to be cut back first, but not
below 50% of the total Firm Shares offered.



June 19, 2002
Page 2


         5. The parties hereby mutually waive any notices required under Section
3(a) and 3(b) of the Registration Rights Agreement.

         6. The Registration will be deemed a Demand Registration for purposes
of Section 14 of the Registration Rights Agreement.

         7. Notwithstanding Section 3(e) of the Registration Rights Agreement,
the Company will not withdraw or decline to file the Registration without the
consent of the Foundation, which consent will not be unreasonably withheld.
However, the Company will not be required to participate in the offering with
its primary issue shares except upon terms and conditions acceptable to the
Company in its discretion. If the Company withdraws from the offering after the
filing of the Registration Statement with the Securities and Exchange
Commission, and the Foundation continues with the sale of its shares that are
subject to the Registration Statement, the Company agrees to participate in the
marketing of the offer and sale of the Foundation's shares with appropriate
personnel and further agrees to pay all costs and expenses in connection with
the marketing of the offer and sale of such shares including, but not limited
to, expenses associated with the production of road show slides and graphics,
fees and expenses of any consultants engaged in connection with road show
presentations, travel, lodging and related expenses, but excluding any
underwriting discounts and commissions and transfer taxes relating to the sale
or disposition of such shares pursuant to the Registration Statement and any
fees, expenses or disbursements of counsel and other advisors to the Foundation.

         8. In all other respects, the above described registration shall be
deemed to be a "Piggy-Back" registration pursuant to Section 3 of the
Registration Rights Agreement, and all the other provisions of the Registration
Rights Agreement shall govern the offering and sale of the shares described
herein.

         Please confirm that the foregoing correctly sets forth the agreement
between us.

                                               Very truly yours,

                                               COBALT CORPORATION


                                               By:    /s/  Gail L. Hanson
                                                   ---------------------------


Confirmed:

Wisconsin United for Health Foundation, Inc.


By:    /s/  David G. Meissner, v.p.
    -------------------------------------