How have post-career transitions into and out of self-employment been impacted by the Great Recession? Research from the 1990s and 2000s has shown that the prevalence of self employment increases substantially later in life, partly because self employment provides older workers with opportunities and flexibility not found in wage-and-salary jobs. Post-career transitions into and out of self employment have also been identified as an important pathway to retirement among older Americans. This paper examines post-career self-employment transitions during the recent recession that began in late 2007 and during the ensuing lackluster recovery. We utilize the Health and Retirement Study (HRS), a nationally-representative longitudinal dataset of older Americans, to investigate the role of self-employment in the retirement transitions of HRS Core respondents over nearly two decades, from 1992 to 2010, with particular emphasis on the most recent years. We find that post-career transitions into and out of self employment remain common in the face of the Great Recession, and that health status, occupation, and financial variables continue to be important determinants of switches from wage-and-salary career employment to self-employed bridge jobs. The latest evidence confirms that self employment continues to be an important pathway to retirement even during recessionary times.