Exhibit 99.1

AFFIRMATIVE INSURANCE HOLDINGS REPORTS SECOND QUARTER 2011

FINANCIAL RESULTS

ADDISON, Texas, August 15, 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 six months ended June 30, 2011.

Gary Kusumi, Chief Executive Officer, stated, “Our second quarter results demonstrate continued progress as a result of actions taken with respect to pricing, underwriting, expense reduction and claims. Although we have not yet achieved overall profitability, two consecutive quarters of positive trends are encouraging. We introduced our new multi-variate (segmented) product in three of our largest states, Louisiana, Texas and Alabama, in the second quarter and expect to roll-out the product in Illinois, another major state for us, by year’s end. Although these trends are positive and establish a foundation for success in the future, we remain concerned about premium levels. Our plan anticipated a significant reduction in premium volume as we increased rates; however, continuing difficult macro-economic conditions may affect our customers’ financial ability to purchase insurance from us. To address this concern, we continue to closely monitor our prices to ensure we are competitive in the marketplace while maintaining our profit margin objective. We also are focused on actively marketing our segmented product aggressively to new customers. While the macro-economic environment likely will present short-term challenges, I remain confident that the actions we have taken and the changes we are making will lead to continued improved financial performance.”

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)