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Previous work suggests that Quantified-Self applications can retain long-term usage with motivational methods. These methods often require intermittent attention requests with manual data input. This may cause unnecessary burden to the user, leading to annoyance, frustration and possible application abandonment. We designed a novel method that uses on-screen alert dialogs to transform recurrent smartphone usage sessions into moments of data contributions and evaluate how accurately machine learning can reduce unintended interruptions. We collected sensor data from 48 participants during a 4-week long deployment and analysed how personal device usage can be considered in scheduling data inputs. We show that up to 81.7% of user interactions with the alert dialogs can be accurately predicted using user clusters, and up to 75.5% of unintended interruptions can be prevented and rescheduled. Our …