Research is needed that describes how the COVID-19 pandemic affected the employment of autistic youth. In this mixed-methods study, we present data on three cohorts of military-connected/dependent youth on the autism spectrum participating in a randomized, waitlist-controlled trial of Project SEARCH + ASD Supports to describe the potential effects of COVID-19 on employment. We also present three participant case studies to highlight challenges and opportunities faced during the transition process. Findings indicate the pandemic appeared to affect the 2019-2020 cohort most negatively, with employment outcomes lagging the previous cohorts by 29.1% to 48.2%. However, the case studies highlight approaches that effectively supported participants, including interagency collaboration, military and federal partnerships, skilled employment specialist support, and family involvement.