Abstract Weight losses >10% favorably modulate biomarkers of breast cancer risk but are not typically achieved by comprehensive weight loss programs, including the Diabetes Prevention Program (DPP). Combining the DPP with hunger training (HT), an evidence-based self-regulation strategy that uses self-monitored glucose levels to guide meal timing, has potential to enhance weight losses and cancer-related biomarkers, if proven feasible. This two-arm randomized controlled trial examined the feasibility of adding HT to the DPP and explored effects on weight and metabolic and breast cancer risk biomarkers. Fifty postmenopausal women [body mass index (BMI) >27 kg/m2)] at risk of breast cancer were randomized to the DPP+HT or DPP-only arm. Both arms followed a 16-week version of the DPP delivered weekly by a trained registered dietitian. Those in the DPP+HT also wore a continuous glucose monitor during weeks 4–6 of the program. Feasibility criteria were accrual rates >50%, retention rates >80%, and adherence to the HT protocol >75%. All a priori feasibility criteria were achieved. The accrual rate was 67%, retention rate was 81%, and adherence to HT was 90%. Weight losses and BMI reductions were significant over time as were changes in metabolic and breast cancer risk biomarkers but did not vary by group. This trial demonstrated that HT was feasible to add to comprehensive weight management program targeted toward postmenopausal women at high risk of breast cancer, though upon preliminary examination it does not appear to enhance weight loss or metabolic changes. Prevention Relevance: This study found that it was feasible to add a short glucose-guided eating intervention to a comprehensive weight management program targeting postmenopausal women at high risk of breast cancer. However, further development of this novel intervention as a cancer prevention strategy is needed.