AMENDMENT NO. 21 TO SERVICES AGREEMENT NUMBER 1

Exhibit 10.1

AMENDMENT NO. 21 TO SERVICES AGREEMENT NUMBER 1

This Amendment No. 21 (this “Amendment”) amends Services Agreement Number 1 (the “Services Agreement”) entered into by and between Affirmative Insurance Holdings, Inc., a Delaware corporation (“Client” or “Affirmative”) and Accenture LLP, an Illinois limited liability partnership (“Accenture” or “ACN”), as amended (the “Services Agreement”), which is subject to the Master Services Agreement entered into between Client and Accenture on October 16, 2006 (“Master Agreement” or “MSA”), as amended, incorporated herein by reference. This Amendment shall be deemed effective as of May 15, 2013 (the “Amendment Effective Date”).

WHEREAS, a dispute has arisen between the Parties in connection with amounts due under the Services Agreement;

WHEREAS, Affirmative has exercised its right to terminate the Services Agreement for convenience in accordance with Section 17.3 of the MSA, Section 10 of the Services Agreement, and the terms set forth in this Amendment;

WHEREAS, the Services Agreement is the only applicable services agreement between the Parties under the MSA, and therefore, termination of the Services Agreement shall result in the simultaneous termination of the MSA pursuant to Section 2.1 of the MSA;

WHEREAS, the Parties agree and represent that they have satisfied the necessary requirements of Section 18 of the MSA for Dispute Resolution in relation to any claims regarding such termination for convenience of the MSA and the Services Agreement; and

WHEREAS, Accenture and Affirmative desire to capture their mutual agreement, as further set forth below, to amend the terms and conditions of the Amended Services Agreement, to modify the services to be provided pursuant to the Services Agreement, and to resolve a dispute between Affirmative and Accenture in connection with amounts due under the Services Agreement.

NOW, THEREFORE, for good and valuable consideration, the receipt and adequacy of which is hereby acknowledged, the parties agree to the following changes:

The Services Agreement is amended as of the Amendment Effective Date as follows:

The Parties agree that this revised payment schedule reflects (i) the outstanding balance due to Accenture for the IO and AO Services provided under the Services Agreement, (ii) estimated amounts due for Termination Assistance Services to be provided through the Termination Assistance Services Completion Date, and (iii) the Termination Amounts required to be paid by Affirmative to exercise its right to terminate the Services Agreement for convenience. The Parties further agree that the Estimated Monthly Payments may vary based on the actual Termination Assistance Services Fees (including any applicable Pass-Through Expenses) incurred in rendering the Termination Assistance Services through the Termination Assistance Services Completion Date. This revised payment schedule supersedes and replaces any term in the Services Agreement or MSA to the contrary, including but not limited to Schedule 5 (Pricing) and Schedule 8 (Termination Amounts Schedule).

Accenture shall invoice Affirmative for the Monthly Payments each month as set forth in Section 10.7 of the MSA, consistent with the terms of this Amendment and the revised payment schedule, which invoices shall reflect the actual Termination Assistance Services Fees. Provided that Affirmative makes payment of all undisputed invoices issued in accordance with the terms of this Amendment and the revised payment schedule, Accenture shall release Affirmative from all further payment obligations pursuant to the Services Agreement and MSA.

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IN WITNESS WHEREOF, the Parties hereto have signed this Amendment as of the dates below and such Amendment is effective as of the Effective Date.