Background: The Assistant to Lift your Level of activitY (Ally) app is a smartphone application that combines financial incentives with chatbot-guided interventions to encourage users to reach personalized daily step goals. Purpose: To evaluate the effects of incentives, weekly planning, and daily self-monitoring prompts that were used as intervention components as part of the Ally app. Methods: We conducted an 8 week optimization trial with n = 274 insurees of a health insurance company in Switzerland. At baseline, participants were randomized to different incentive conditions (cash incentives vs. charity incentives vs. no incentives). Over the course of the study, participants were randomized weekly to different planning conditions (action planning vs. coping planning vs. no planning) and daily to receiving or not receiving a self-monitoring prompt. Primary outcome was the achievement of personalized daily step goals. Results: Study participants were more active and healthier than the general Swiss population. Daily cash incentives increased step-goal achievement by 8.1%, 95% confidence interval (CI): [2.1, 14.1] and, only in the no-incentive control group, action planning increased step-goal achievement by 5.8%, 95% CI: [1.2, 10.4]. Charity incentives, self-monitoring prompts, and coping planning did not affect physical activity. Engagement with planning interventions and self-monitoring prompts was low and 30% of participants stopped using the app over the course of the study. Conclusions: Daily cash incentives increased physical activity in the short term. Planning interventions and self-monitoring prompts require revision before they can be included in future versions of the app. Selection effects and engagement can be important challenges for physical-activity apps.