Within an academic health system in the United States that already performs electronic health record-based sugary drink screening, we conducted a pilot randomized trial of a technology-driven family beverage choice intervention. The goal of the intervention was to reduce sugar-sweetened beverage (SSB) and fruit juice (FJ) consumption in 60 parent–child dyads, in which children were 1–8 years old. The pediatrician-initiated intervention consisted of a water promotion toolkit, a video, a mobile phone application, and 14 interactive voice-response phone calls to parents over 6 months. The study was conducted between June 2021 and May 2022. The aim of the pilot study was to assess the potential feasibility and efficacy of the newly developed intervention. Intervention fidelity was excellent, and acceptability was high for all intervention components. Children in both the intervention and the control groups substantially decreased their consumption of SSB and FJ over follow-up (mean combined baseline 2.5 servings/day vs. 1.4/day at 6 months) and increased water consumption, but constrained linear mixed-effects models showed no differences between groups on these measures. Compared to parents in the control group, intervention parents had larger decreases in SSB intake at 3 months (−0.80 (95% CI: −1.54, −0.06, p = 0.03) servings daily), but these differences were not sustained at 6 months. These findings suggest that, though practical to implement in a clinical care setting and acceptable to a diverse participant group, our multicomponent intervention may not be universally necessary to achieve meaningful behavior changes around family beverage choice. A lower-intensity intervention, such as EHR-based clinical screening alone, might be a less resource-intense way for health systems to achieve similar behavioral outcomes. Future studies might therefore explore whether, instead of applying a full intervention to all families whose children overconsume SSB or FJ, a stepped approach, starting with clinical screening and brief counseling, could be a better use of health system resources.