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The number of smartphone users worldwide is rapidly rising. However, there are only few and contradictory scientific findings about the users’ well-being in the context of smartphone use. The most popular applications are instant messengers (IM). Our study aims to understand under which conditions IM is related to stress. Based on Self-Determination Theory, we assumed that an autonomous motivation to use IM is associated with less stress. Furthermore, inferred from research on the relationship of mindfulness with well-being, we suspected a negative relationship between mindfulness during IM and stress. Finally, we hypothesized that a day-specific mindfulness might indirectly reduce stress by empowering people to use their devices more autonomously. We conducted a diary study with 211 participants who answered 868 short questionnaires on five consecutive days. The results of regression analyses supported our assumptions. We discuss implications of our findings and further methods of analyses.