Background: Globally, rising trends in gestational diabetes and body mass index contribute to maternal and neonatal morbidity and mortality. Lifestyle modifications and breastfeeding may reverse this effect, although few studies combine these into one intervention. Research Aims: To measure postpartum weight retention, breastfeeding duration, hemoglobin A1C, and mean arterial blood pressure at 6 months postpartum among women with elevated pre-pregnancy body mass index. Methods: The electronic Monitoring of Mom’s Schedule study (eMOMS™) was a feasibility, three-arm, randomized controlled trial modeled after a Diabetes Prevention Program and breastfeeding support. A health coach delivered a 12-month virtual intervention. Study arm results were compared using Wilcoxon signed-ranks exact test reporting from a two-sided test and bootstrapped samples with 95% confidence intervals. Results: Between September 2019 and May 2021, 100 individuals were screened, and 35 were randomized: nine to Group 1, 14 to Group 2, and 12 to Group 3. At baseline, participants averaged 13.0 (SD = 2.5) weeks gestation, with a mean pre-pregnancy body mass index of 29.7 (SD = 3.0). With 5,000 bootstrapped samples, mean weight retention from baseline to 6 months postpartum was: 4.0 kg, 95% CI [1.6, 6.2] for Group 1; 3.7 kg, CI [-1.8, 9.8] for Group 2; and 7.5 kg, CI [4.1, 11.6] for Group 3. Mean (exclusive) breastfeeding duration was 9.3 weeks, 95% CI [0.43, 26.1]; 9.6 weeks, CI [4.4, 15.7]; and 15.1 weeks, CI [6.5, 23.3] for each group, respectively. Conclusion: Our intervention was positively associated with postpartum weight retention and breastfeeding duration. Future research is needed to assess intervention components. © The Author(s) 2024.