Exhibit 99.1

AFFIRMATIVE INSURANCE HOLDINGS REPORTS THIRD QUARTER 2011 FINANCIAL RESULTS

ADDISON, Texas, November 14, 2011 (GLOBE NEWSWIRE) — Affirmative Insurance Holdings, Inc. (Nasdaq:AFFM), a leading distributor and producer of non-standard personal automobile insurance policies, reported consolidated financial results for the three and nine months ended September 30, 2011.

Gary Kusumi, Chief Executive Officer, stated, “Third quarter results were primarily driven by reduced premium volume in our largest states. While the pricing, underwriting, expense and claims initiatives we have undertaken are positioning us for long-term growth and profitability, revenue generation continues to be our greatest short-term challenge. To address this challenge, we are taking a number of specific steps. First, we continue to review our price competitiveness on a state-by-state basis. Second, we continue to focus on our local marketing initiatives and agent quote generation. We believe these efforts combined with our multi-variate, segmented product and competitive forces will produce increased premium for the Company in 2012. While we expect to face continued macro-economic headwind in the short-term, I remain confident in the Company’s ability to produce a sustainable competitive advantage in the fragmented non-standard market.”

Operating Performance

About Affirmative

Affirmative Insurance Holdings, Inc. is a distributor and producer of non-standard personal automobile insurance policies and related products and services for individual consumers in targeted geographic markets. Non-standard personal automobile insurance policies provide coverage to drivers who find it difficult to obtain insurance from standard automobile insurance companies due to their lack of prior insurance, age, driving record, limited financial resources or other factors. Non-standard personal automobile insurance policies generally require higher premiums than standard automobile insurance policies.

This press release contains forward-looking statements made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. Forward-looking statements may be identified by, among other things, the use of forward-looking terms such as “likely,” “typically,” “may,” “intends,” “expects,” “believes,” “anticipates,” “estimates,” “projects,” “targets,” “forecasts,” “seeks,” “potential,” , or “attempts” or the negative of such terms or other variations on such terms or comparable terminology. By their nature, these statements are subject to risks, uncertainties and other factors, which could cause actual future results to differ materially from those results expressed or implied by such forward-looking statements.

Do not unduly rely on forward-looking statements. They give the Company’s expectations about the future and are not guarantees. Forward-looking statements speak only as of the date they are made, and, except as required by law, the Company does not intend to update them to reflect changes that occur after that date. For a discussion of factors that may cause actual results to differ from expectations, refer to the Company’s filings with the Securities and Exchange Commission, including its Annual Report on Form 10-K for the year ended December 31, 2010. Any factor described in this press release or in any document referred to in this press release could, by itself or together with one or more other factors, adversely affect the Company’s business, earnings and/or financial condition.

AFFIRMATIVE INSURANCE HOLDINGS, INC. AND SUBSIDIARIES

CONSOLIDATED STATEMENTS OF INCOME (LOSS)

(in thousands, except per share data)