Abstract Obesity is remarkably refractory to treatment. Despite a plethora of quantitative studies, little qualitative research has been conducted on the topic of weight loss maintenance. This study used six focus groups to explore which factors promoted or prevented maintaining weight loss among a diverse, urban population. Eligible participants were those who had intentionally lost ≥10% of their body weight in the past 2 years and were categorized as either “regainers” or “maintainers” using self-reported length of weight maintenance and amount (%) regained. Regainers had regained ≥33% of their weight loss and maintainers had regained ≤15%. Participants (n=29) were predominantly African-American (58.6%) females (65.6%) with a mean age of 46.9±11.2 years. Four themes reflected similarities between regainers and maintainers, and four reflected differences between the groups. Both groups experienced lapses, used clothing fit for feedback on weight status, desired greater support during maintenance, and decreased self-monitoring of food intake over time. When compared with regainers, maintainers more often continued strategies used during weight loss, weighed themselves regularly, and used productive problem-solving skills and positive self-talk. Regainers experienced greater difficulty independently continuing food and exercise behaviors during maintenance, identifying decreased accountability and waning motivation as barriers. These findings suggest that weight loss maintenance efforts can be improved by addressing challenges such as long-term self-monitoring and problem-solving skills, and that maintenance success might depend on how people think as much as what they do.