Interventions have modest impact on reducing excessive gestational weight gain (GWG) in pregnant women with overweight/obesity. This two-arm feasibility randomized control trial tested delivery of and compliance with an intervention using adapted dosages to regulate GWG, and examined pre-post change in GWG and secondary outcomes (physical activity: PA, energy intake: EI, theories of planned behavior/self-regulation constructs) compared to a usual care group. Pregnant women with overweight/obesity (N = 31) were randomized to a usual care control group or usual care + intervention group from 8 to 2 weeks gestation and completed the intervention through 36 weeks gestation. Intervention women received weekly evidence-based education/counseling (e.g., GWG, PA, EI) delivered by a registered dietitian in a 60-min face-to-face session. GWG was monitored weekly; women within weight goals continued with education while women exceeding goals received more intensive dosages (e.g., additional hands-on EI/PA sessions). All participants used mHealth tools to complete daily measures of weight (Wi-Fi scale) and PA (activity monitor), weekly evaluation of diet quality (MyFitnessPal app), and weekly/monthly online surveys of motivational determinants/self-regulation. Daily EI was estimated with a validated back-calculation method as a function of maternal weight, PA, and resting metabolic rate. Sixty-five percent of eligible women were randomized; study completion was 87%; 10% partially completed the study and drop-out was 3%. Compliance with using the mHealth tools for intensive data collection ranged from 77 to 97%; intervention women attended > 90% education/counseling sessions, and 68–93% dosage step-up sessions. The intervention group (6.9 kg) had 21% lower GWG than controls (8.8 kg) although this difference was not significant. Exploratory analyses also showed the intervention group had significantly lower EI kcals at post-intervention than controls. A theoretical, adaptive intervention with varied dosages to regulate GWG is feasible to deliver to pregnant women with overweight/obesity.