Mobile health applications for weight maintenance offer self-monitoring as a tool to empower users to achieve health goals (e.g., losing weight); yet maintaining consistent self-monitoring over time proves challenging for users. These apps use push notifications to help increase users’ app engagement and reduce long-term attrition, but they are often ignored by users due to appearing at inopportune moments. Therefore, we analyzed whether delivering push notifications based on time alone or also considering user context (e.g., current activity) affected users’ engagement in a weight maintenance app, in a 4-week in-the-wild study with 30 participants. We found no difference in participants’ overall (across the day) self-monitoring frequency between the two conditions, but in the context-based condition, participants responded faster and more frequently to notifications, and logged their data more timely (as eating/exercising occurs). Our work informs the design of notifications in weight maintenance apps to improve their efficacy in promoting self-monitoring.