Background Just-in-time adaptive interventions (JITAIs) provide real time in-the-moment behavior change support to people when they need it most. JITAIs could be a viable way to provide personalized physical activity (PA) support to older adults in the community. However, it is unclear how feasible it is to remotely deliver a PA intervention through a smartphone to older adults or how acceptable they would find a JITAI targeting PA in everyday life. Objective The aims of this study are to describe the development of JitaBug, a personalized smartphone-delivered JITAI designed to support older adults to increase or maintain their PA level, assess the feasibility of conducting an effectiveness trial of the JitaBug intervention, and explore the acceptability of JitaBug among older adults in a free-living setting. Methods The intervention was developed using the Behavior Change Wheel and consisted of a wearable activity tracker (Fitbit) and a companion smartphone app (JitaBug) that delivered goal-setting, planning, reminders, and JITAI messages to encourage achievement of personalized PA goals. Message delivery was tailored based on time of day, real time PA tracker data, and weather conditions. We tested the feasibility of remotely delivering the intervention with older adults in a 6-week trial. Data collection involved assessment of PA through accelerometery and activity tracker, self-reported mood and mental well-being through ecological momentary assessment, and contextual information on PA through voice memos. Feasibility outcomes included recruitment capability and adherence to the intervention, intervention delivery in the wild, appropriateness of data collection methodology, adverse events, and participant satisfaction. Results Of the 46 recruited older adults (aged 56-72 years), 31 (67%) completed the intervention. The intervention was successfully delivered as intended; 87% (27/31) of the participants completed the intervention independently; 94% (2247/2390) of the PA messages were successfully delivered; 99% (2239/2261) of the Fitbit and 100% (2261/2261) of the weather data calls were successful. Valid and usable wrist-worn accelerometer data were obtained from 90% (28/31) of the participants at baseline and follow-up. On average, the participants recorded 50% (7.9/16, SD 7.3) of the voice memos, 38% (3.3/8, SD 4.2) of the mood assessments, and 50% (2.1/4, SD 1.6) of the well-being assessments through the app. Overall acceptability of the intervention was very good (23/30, 77% expressed satisfaction). Participant feedback suggested that more diverse and tailored PA messages, app use reminders, technical refinements, and an improved user interface could improve the intervention and make it more appealing. Conclusions This study suggests that a smartphone-delivered JITAI is an acceptable way to support PA in older adults in the community. Overall, the intervention is feasible; however, based on user feedback, the JitaBug app requires further technical refinements that may enhance use, engagement, and user satisfaction before moving to effectiveness trials.