SummaryDue to insufficient treatment options for insomnia, effective solutions are urgently needed. We evaluated the effects of a CBT‐I‐based app combining sleep training with subjective and objective sleep monitoring on (i) sleep and (ii) subjective‐objective sleep discrepancies (SOSD). Fifty‐seven volunteers (20–76 years; MAge = 45.67 ± 16.38; 39 female) suffering from sleep problems were randomly assigned to an experimental group (EG, n = 28) or a waitlist control group (CG, n = 29). During the 6‐week app phase, the EG used the CBT‐I‐based programme and a heart rate sensor for daily sleep monitoring and ‐feedback, while the CG used sleep monitoring only. Sleep was measured (i) subjectively via questionnaires (Insomnia Severity Index, ISI; Pittsburgh Sleep Quality Index, PSQI), (ii) objectively via ambulatory polysomnography (PSG), and (iii) continuously via heart‐rate sensor and sleep diaries. Data revealed interactions for ISI (p = 0.003, ƞ2part = 0.11) and PSQI (p = 0.050, ƞ2part = 0.05), indicating training‐specific improvements in EG, yet not in CG. While PSG‐derived outcomes appear to be less training‐specific, a tendential reduction in wake after sleep onset (WASO) was found in EG (p = 0.061, d = 0.55). Regarding changes in SOSD, the results indicate improvements during the app phase (EG) for sleep efficiency, sleep onset latency, and WASO (p ≤ 0.022, d ≥ 0.46); for total sleep time both groups showed a SOSD reduction. The findings indicate beneficial effects of a novel smartphone app on sleep and SOSD. More scientific evaluation of such digital programmes is needed to ultimately help in reducing the gap in non‐pharmacological insomnia treatment.