This paper presents qualitative findings from two field studies that focused on supporting people with sleeplessness (Study I) and moderate depression (Study II). Both the studies were designed to examine the potential impact of reminders and rehearsal on the effectiveness of web-based information systems that were developed by implementing selected persuasive software features and incorporated with Acceptance and Commitment Therapy-based exercises. Sleeplessness and moderate depression were chosen because first, they are interrelated and, second they are essential for an individual’s general wellbeing. Good quality of life depends on different factors, and both sleeplessness and depression, if not addressed, can have detrimental consequences. In this paper, qualitative findings are reported with an aim to highlight underlying issues that are at times ignored. Further, the findings are expected to help designers better understand the dynamics of information systems that are developed for mental healthcare. For data collection, we used semi-structured interviews and Likert-scale questionnaires. Although, we used SPSS Version 20 to perform statistical analyses on pre- and post- study psychological measures for both Study I and II, however in this paper only qualitative findings will be reported as in the context of healthcare- related research qualitative methodologies have been advocated as a constructive approach. The results from the two studies portray an interesting contrast. While the participants of the Study I (Sleeplessness) did not generally find reminders to be effective, on the contrary, the participants of study II (Depression) highly appreciated reminders especially in terms of task completion. In terms of rehearsal, participants from both the studies favoured the software feature for learning new behaviors. Based on the qualitative findings, we have identified six emerging themes that are expected to open further research opportunities for mental healthcare researchers.