<p>Chronic insomnia is a prevalent disorder that negatively impacts Veterans’ health. The first-line intervention is cognitive behavioral therapy for insomnia (CBT-I); however, sleep medications, which have unreliable effectiveness and pose risks for adverse events, are the most commonly used intervention. Pairing CBT-I with deprescribing (the supervised reduction of medications) can enhance medication reduction outcomes and reduce rebound insomnia. This pilot trial tests the parallel delivery of Clinical Pharmacy Practitioner (CPP) deprescribing and a digital clinical decision support (CDS) platform assisting clinician-supervised asynchronous CBT-I (A-CBT-I). In this nonrandomized, single-arm trial conducted at VA Pittsburgh Healthcare System, we assessed the acceptability, usability, and clinical impact of CPP-led deprescribing delivered in parallel with digital A-CBT-I over 12&#xa0;weeks in Veterans who were taking sleep medications (e.g., trazodone, zolpidem) before enrollment for at least 3&#xa0;months. The A-CBT-I included stimulus control, time in bed restriction, cognitive restructuring, and relaxation. Sleep medication dose and frequency, medication reduction-related side-effects, and symptom measures were tracked through the CDS platform. Medication reduction was personalized through shared decision-making, targeting cessation or a stable reduced dose and/or frequency. Veteran self-reported outcomes included medication dose and frequency, Insomnia Severity Index (ISI), and Patient-Reported Outcome Measurement Information System (PROMIS) measures for sleep disturbance, pain, physical function, and social roles. Veterans also rated the CDS platform’s usefulness, information quality, and interface quality using the Post-Study System Usability Questionnaire (PSSUQ). Forty-two Veterans enrolled and 36 downloaded the CDS platform app. Participants were mostly male (92%) and white (86%), with an average age of 59&#xa0;years. Veterans significantly reduced their sleep medication average daily dose from baseline to post-treatment (T0-T1; <i>p</i> &lt; 0.004) and baseline to 3-month follow-up (T0-T2; <i>p</i> &lt; 0.005). Thirty-two percent of Veterans stopped using sleep medications by T1 (<i>p</i> = 0.052) and 60% had stopped by T2 (<i>p</i> &lt; 0.001). ISI improved significantly T0-T1 and T0-T2 (<i>p</i>s&lt; 0.001). PROMIS for sleep disturbance, pain, physical and cognitive function, and social roles also significantly improved (T0-T1/T0-T2; <i>p</i>s &lt; 0.001–0.05). Veterans rated the CDS platform highly, per the PSSUQ, on system usefulness, information quality, and interface quality. Results suggest that a CDS platform supporting digital A-CBT-I delivered in parallel with CPP-led deprescribing is a feasible and promising approach to reduce sleep medications and improve insomnia symptoms and related outcomes among Veterans. Larger clinical trials (e.g., randomized, pragmatic, and/or hybrid implementation-effectiveness) with more diverse patient populations are needed to confirm effectiveness, efficiency, and to identify potential barriers and facilitators to implementing in routine clinical practice.</p><p>&#xa0;<i>Trial Registration</i>ClinicalTrials.gov NCT05027438.</p>