Appropriate amount and good quality of sleep are essential for mental and general well-being. Sleep deprivation and other chronic sleep disorders could lead to negative consequences for health, poor quality of life and reduced competence. An individual’s quality of life could be unsettled because of several reasons, sleep deprivation is one of them. Information systems (IS) and human-computer interaction (HCI) researchers have paid considerable attention to promote healthy behaviors however sleep deprivation as a problem domain has received relatively little attention. In this paper, we present qualitative findings from a field study that examined potential influence of persuasive reminders and virtual rehearsal on the effectiveness of a Behavior Change Support System (BCSS). Tyyne is a BCSS developed for people suffering from sleep deprivation. The content of virtual rehearsal modules were drawn from Acceptance and Commitment Therapy. Participants were recruited through newspaper advertisements. After screening at the university clinic, eligible participants (n = 86) were randomized into an Intervention group and a Control (wait-list) group. For data collection, we employed pre and post study structured questionnaires. Upon completion of the study, 41 participants volunteered to complete post study questionnaires. The findings reveal that a moderate number of participants (60.5%) improved their sleeping habits, a significantly high number of participants (79.1%) approved the BCSS, a staggering high number (93.0%) of the participants agreed that learning new skills through web-based BCSS is a good idea, and a substantial number of participants (72.1%) believed that persuasive reminders help people in task completion and compliance. Even though only about one third of participants (37.2%) reported that after using the BCSS they could better manage their sleep disorders, we suggest that the findings are encouraging. Given that treating sleep deprivation requires much longer periods of time than the intervention’s duration (in our case it was 6 weeks), improvement with one third of the participants is nevertheless a promising result. On the whole, persuasive reminders and virtual rehearsal as software features have a significant potential to enhance overall effectiveness of information systems for chronic sleep disorders.