Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

On June 30, 2009, the Registrant and M. Sean McPadden mutually agreed to terminate Mr. McPadden's employment with the Registrant effective July 30, 2009. Accordingly, Mr. McPadden has resigned his position as the Registrant's Executive Vice President, Chief Underwriting Officer and President of the Registrant's insurance company subsidiaries effective June 30, 2009. The functions of the Registrant's Claims, Business Development and Product Management business units as previously managed by Mr. McPadden will report directly to the Registrant's Chief Executive Officer, Kevin R. Callahan, and the functions of the Registrant's Actuarial business unit will report directly to the Registrant's Chief Financial Officer, Michael McClure, on a going forward basis.

Item 8.01 Other Events.

On July 7, 2009, the Registrant issued a press release entitled "Affirmative Insurance Holdings Reports Several Recent Actions" wherein the Registrant reported that: (i) the exact amount of the pretax charge in connection with the termination of M. Sean McPadden's employment, while not finalized, is expected to be approximately $1 million, (ii) the Registrant sold all of its retail stores and franchise operations in the State of Florida, (iii) effective July 25, 2009, the Registrant will suspend its employer contributions to its 401(k) plan, and (iv) due to the deteriorating overall nature of the current economic environment, the Registrant is presently examining the possible implementation of certain organizational changes, including: (1) consolidating insurance operations into one location, (2) evaluating both agency and claims operations to identify certain consolidation opportunities, and (3) conducting a general business unit review to identify and implement additional expense savings opportunities. The Registrant further reported that it expects that the cumulative effect of the foregoing actions will result in a savings of approximately $10 million annually and the elimination of approximately 150 jobs.

Item 9.01. Financial Statements and Exhibits.

(d) Exhibits:

99.1 Press Release dated July 7, 2009, entitled "Affirmative Insurance Holdings Reports Several Recent Actions".