Background Detailed self-monitoring (or tracking) of dietary intake is a popular and effective weight loss approach that can be delivered via digital tools, although engagement declines over time. Simplifying the experience of self-monitoring diet may counteract this decline in engagement. Testing these strategies among racial and ethnic minority groups is important as these groups are often disproportionately affected by obesity yet underrepresented in behavioral obesity treatment. Objective In this 2-arm pilot study, we aimed to evaluate the feasibility and acceptability of a digital weight loss intervention with either detailed or simplified dietary self-monitoring. Methods We recruited racial and ethnic minority adults aged ≥21 years with a BMI of 25 kg/m2 to 45 kg/m2 and living in the United States. The Pacific time zone was selected for a fully remote study. Participants received a 3-month stand-alone digital weight loss intervention and were randomized 1:1 to either the detailed arm that was instructed to self-monitor all foods and drinks consumed each day using the Fitbit mobile app or to the simplified arm that was instructed to self-monitor only red zone foods (foods that are highly caloric and of limited nutritional value) each day via a web-based checklist. All participants were instructed to self-monitor both steps and body weight daily. Each week, participants were emailed behavioral lessons, action plans, and personalized feedback. In total, 12 a priori benchmarks were set to establish feasibility, including outcomes related to reach, retention, and self-monitoring engagement (assessed objectively via digital tools). Acceptability was assessed using a questionnaire. Weight change was assessed using scales shipped to the participants’ homes and reported descriptively. Results The eligibility screen was completed by 248 individuals, of whom 38 (15.3%) were randomized, 18 to detailed and 20 to simplified. At baseline, participants had a mean age of 47.4 (SD 14.0) years and BMI of 31.2 (SD 4.8) kg/m2. More than half (22/38, 58%) were identified as Hispanic of any race. The study retention rate was 92% (35/38) at 3 months. The detailed arm met 9 of 12 feasibility benchmarks, while the simplified arm met all 12. Self-monitoring engagement was moderate to high (self-monitoring diet: median of 49% of days for detailed, 97% for simplified; self-monitoring steps: 99% for detailed, 100% for simplified; self-monitoring weight: 67% for detailed, 80% for simplified). Participants in both arms reported high satisfaction, with 89% indicating that they would recommend the intervention. Weight change was −3.4 (95% CI −4.6 to −2.2) kg for detailed and −3.3 (95% CI −4.4 to −2.2) kg for simplified. Conclusions A digital weight loss intervention that incorporated either detailed or simplified dietary self-monitoring was feasible, with high retention and engagement, and acceptable to racial and ethnic minority adults. Trial Registration ASPREDICTED #66674; https://aspredicted.org/ka478.pdf