The aim of this study was to identify predictors of weight regain and continued weight maintenance among individuals already successful at long-term weight loss in a widely available weight-management program. Participants were 2843 weight-loss maintainers in WeightWatchers who had maintained weight loss ≥9.1 kg for ≥1 year (average 25.5 kg for 3.5 years; BMI = 26.7 kg/m2 ). Validated behavioral, psychosocial, and home environmental questionnaires were administered at study entry and 1 year later. Discriminant analysis identified variables that discriminated gainers (≥2.3-kg gain) from maintainers (±2.3-kg change). Over the 1 year of follow-up, 43% were gainers (mean [SD], 7.2 [5.4] kg), and 57% were maintainers (0.4 [1.2] kg). Compared with maintainers, gainers were younger and had higher initial weight, more recent weight losses, and larger initial weight losses. Standardized canonical coefficients indicated that the 1-year changes that most discriminated gainers from maintainers were greater decreases in the ability to accept uncomfortable food cravings, urges, and desires to overeat (0.232); self-monitoring (0.166); body image (0.363); and body satisfaction (0.194) and greater increases in disinhibition (0.309) and bodily pain (0.147). The canonical correlation was 0.505 (p < 0.001). Future interventions to prevent regain should consider targeting overeating in response to internal and external food cues and declines in self-monitoring and body image.