Background: Although cognitive behavioral therapy sleep treatments have been shown to be safe, effective, and associated with durable improvements in patients presenting with insomnia (CBTI), they have not been used to promote healthy sleep in military populations that include active duty service members (ADSM), veterans, and the clinicians who serve them. This population's need for CBTI treatments might be best met through the use of interactive Resilience Enhancing Sleep Tactics (iREST), an application developed as a form of just-in-time adaptive intervention (JITAI). Drawing from existing BBTI contexts, iREST could offer ADSM and veterans a more efficacious form of CBTI by dynamically adapting both the assessment and intervention in response to each user's highly individualized context. Objective: This paper seeks to perform a clinical feasibility study that assesses the JITAI application-the iREST app-for delivering behavioral insomnia treatment in a military population. The outcomes are then compared with results from a traditional (in person) behavioral treatment. Methods: In this feasibility study, ADSM and Veterans between the ages of 18 and 60 were recruited and subjected to a set of eligibility and exclusion criteria through a set of surveys, questionnaires, and interviews. Once selected, participants followed the BBTI intervention through the iREST app for 4-6 weeks. The Insomnia Severity Index (ISI) was used as the primary sleep outcome metric; overall sleep quality was assessed using the Pittsburgh Sleep Quality Index (PSQI) and the PSQI Addendum for PTSD (PSQIA). Results: 22 individuals were included in the clinical feasibility study and 19 (86.36%) completed the post-treatment/follow-up assessment. There were no statistically significant demographic differences between participants in the current study (iREST) and the traditional BBTI study. The chi-squared values for response and remission were found to be = 0.34, >0.05 and < 0.91, >0.05 respectively, suggesting that no significant difference exists between the rates in the current trial and the previous BBTI-MV. Pre and post-intervention tests show statistically significant improvement in primary and secondary outcomes, e.g., the mean reduction on the ISI = 10.16, t (18) = 7.40, < 0.01. While a mixed model ANOVA