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Self-monitoring is the cornerstone of many health and wellness persuasive interventions. However, applications designed to promote health and wellness that use this strategy have recorded varying degrees of success. In this study, we investigated why the self-monitoring strategy might work in some contexts and fail in others. We conducted a series of large-scale studies, with a total of 1768 participants, to explore the strengths and weaknesses of the self-monitoring strategy. Our results uncover important strengths and weaknesses that could facilitate or hinder the effectiveness of self-monitoring to promote the health and wellness of its users. The strengths include its tendency to reveal problem behaviours, provide real and concrete information, foster reflection, make people accept responsibility, create awareness and raise users’ consciousness about their health and wellness. Some of the weaknesses include its …