Reduced schedules of dietary self-monitoring are typically recommended after the end of behavioral weight-loss programs; however, there exists little empirical evidence to guide these recommendations. We explored potential thresholds for dietary self-monitoring during a 9-month maintenance period following a 3-month weight-loss program in 74 adults with overweight or obesity (mean [SD] age = 50.7 [10.4] years, BMI = 31.2 [4.5] kg/m2) who were encouraged to self-monitor weight, dietary intake, and physical activity daily and report their adherence to self-monitoring each week via a study website. Greater self-monitoring was correlated with less weight regain for thresholds of ≥3 days/week, with the largest benefit observed for thresholds of ≥5 to ≥6 days/week (all p < 0.05); significant weight gain was observed for thresholds of ≥1 to ≥2 days/week, whereas no change in weight was observed for thresholds of ≥3 to ≥4 days/week, and weight loss was observed with thresholds of ≥5 or more days/week. Results demonstrate that self-monitoring at least 3 days/week may be beneficial for supporting long-term maintenance, although greater benefit (in relation to weight loss) may be realized at thresholds of 5 to 6 days/week. Future research should investigate whether individuals who were randomized to self-monitor at these different thresholds demonstrate differential patterns of weight-loss maintenance.