Eating habits and food craving are strongly correlated with weight status. It is currently not well understood how psychological and behavioral factors influence both weight loss and weight regain. To examine the associations between psychological and behavioral predictors with weight changes and energy intake in a randomized controlled trial on weight loss. The Prevention of Obesity Using Novel Dietary Strategies is a dietary intervention trial that examined the efficacy of 4 diets on weight loss over 2 years. Participants were 811 overweight (body mass index, 25-40.9 kg/m2; age, 30-70 years) otherwise healthy adults. Every 1-point increase in craving score for high-fat foods at baseline was associated with greater weight loss (-1.62 kg, P = .0004) and a decrease in energy intake (r = -0.10, P = .01) and fat intake (r = -0.16, P < .0001) during the weight loss period. In contrast, craving for carbohydrates/starches was associated with both less weight loss (P < .0001) and more weight regain (P = .04). Greater cognitive restraint of eating at baseline was associated with both less weight loss (0.23 kg, P < .0001) and more weight regain (0.14 kg, P = .0027), whereas greater disinhibition of eating was only associated with more weight regain (0.12 kg, P = .01). Craving for high-fat foods is predictive of greater weight loss, whereas craving for carbohydrates is predictive of less weight loss. Cognitive restraint is predictive of less weight loss and more weight regain. Interventions targeting different psychological and behavioral factors can lead to greater success in weight loss.