School vacations disrupt learning continuity and often erode the momentum students need to stay engaged across time; more recently school closures due to the pandemic have produced similar outcomes. When students are not in school for an extended period, breaks in continuity and waning momentum often translate into irregular engagement with learning activities, allowing previously learned skills to grow rusty. The Keep in School Shape (KiSS) Program repurposes online survey software to provide students with convenient and engaging daily reminders and opportunities to maintain the math skills they need for their future studies via text message or email during times when school is not in session. This paper articulates the architectural logic of a low-stakes, voluntary review environment through a bounded design case and advances a set of transferable design commitments that can inform the design of similar interventions.