Chronic disease self-management education (CDSME) programs benefit individuals with chronic diseases, including mental health conditions, by improving health-related outcomes and increasing engagement with the health care system. Recruiting individuals with a history of mental health conditions to participate in CDSME is challenging, particularly in rural, underserved areas. Hence, it is important to understand factors associated with the presence of mental health conditions, and impacts of CDSME on patient engagement. This project identifies individual and program-level characteristics, as well as recruitment characteristics, associated with reporting a history of depression and/or anxiety. It also assesses factors related to program engagement and the relationship between completing CDSME and patient activation. Data were collected during CDSME workshops offered in 2019 in a rural region of New York. Of the 421 enrollees who completed survey instruments, 162 reported a history of depression and/or anxiety. Univariate analyses indicated that those reporting a history of depression and/or anxiety were younger, female, in poorer health, had more comorbidities, were Medicaid beneficiaries, and had lower patient activation scores. They also heard about and signed up for the workshop through the internet at higher rates than those not reporting a history of depression and/or anxiety. Multivariable logistic regression modeling indicated age, self-rated health, and number of comorbidities were independent predictors of reporting a history of depression and/or anxiety. Among CDSME completers, patient activation significantly improved regardless of history of depression and/or anxiety. Engaging individuals with mental health conditions in CDSME requires a multimodal recruitment strategy incorporating electronic marketing and registration.