User satisfaction is a crucial quality indicator in health service provision. Few studies have measured user satisfaction among homeless and formerly homeless individuals, despite the high prevalence of mental health disorders (MHD) in this population. The purpose of this study was to assess overall satisfaction among 455 homeless and formerly homeless individuals who were receiving health and community services, and to identify factors associated with user satisfaction. Data collection occurred between January and September 2017. Study participants were 18 years old or over, with experience of homelessness in the current or recent past. They completed a questionnaire eliciting socio‐demographic information, and data on residential history, service use and satisfaction and health profiles. Multivariate linear analysis was performed on overall satisfaction with health and community services in the previous 12 months. Independent variables were organised as predisposing, enabling and needs factors based on the Gelberg–Andersen Behavioral Model. The mean satisfaction score was 4.11 (minimum: 1; maximum: 5). Variables associated with greater user satisfaction included: older age, residence in permanent housing, common MHD (e.g., depression, anxiety), having a family physician, having a case manager, strong social network, good quality of life and, marginally, male sex and having substance use disorders (SUD). By contrast, frequent users of public ambulatory health services were the most dissatisfied. User satisfaction was more strongly associated with enabling factors. Strategies for improving satisfaction include: promoting more tailored primary care programmes (including family physician) adapted to the needs of this population, better integrating primary care with specialised services including SUD integrated treatment and enhancing continuity of care through the reinforcement of case management services. Further efforts aimed at increasing access to permanent housing with supports, and eliciting more active involvement by relatives and friends may also improve user satisfaction with services, and reduce unnecessary service use.