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Users make hundreds of transactional permission decisions for smartphone applications, but these decisions persist beyond the context in which they were made. We hypothesized that user concern over permissions varies by context, e.g., that users might be more concerned about location permissions at home than work. To test our hypothesis, we ran a 44-participant, 4-week experience sampling study, asking users about their concern over specific application-permission pairs, plus their physical environment and context. We found distinguishable differences in participants’ concern about permissions across locations and activities, suggesting that users might benefit from more dynamic and contextually-aware approaches to permission decision-making. However, attempts to assist users in configuring these more complex permissions should be made with the aim to reduce concern and affective discomfort—not to normalize and perpetuate this discomfort by replicating prior decisions alone.