Background and Objectives: Stroke is a chronic, complex condition that disproportionally affects older adults. Health systems are evaluating innovative transitional care (TC) models to improve outcomes in these patients. The Comprehensive Post-Acute Stroke Services (COMPASS) Study, a large cluster-randomized pragmatic trial, tested a TC model for patients with stroke or transient ischemic attack discharged home from the hospital. The implementation of COMPASS-TC in complex real-world settings was evaluated to identify successes and challenges with integration into the clinical workflow. Research Design and Methods: We conducted a concurrent process evaluation of COMPASS-TC implementation during the first year of the trial. Qualitative data were collected from 4 sources across 19 intervention hospitals. We analyzed transcripts from 43 conference calls with hospital clinicians, individual and group interviews with leaders and clinicians from 9 hospitals, and 2 interviews with the COMPASS-TC Director of Implementation using iterative thematic analysis. Themes were compared to the domains of the RE-AIM framework. Results: Organizational, individual, and community factors related to Reach, Adoption, and Implementation were identified. Organizational readiness was an additional key factor to successful implementation, in that hospitals that were not "organizationally ready" had more difficulty addressing implementation challenges. Discussion and Implications: Multifaceted TC models are challenging to implement. Facilitators of implementation were organizational commitment and capacity, prioritizing implementation of innovative delivery models to provide comprehensive care, being able to address challenges quickly, implementing systems for tracking patients throughout the intervention, providing clinicians with autonomy and support to address challenges, and adequately resourcing the intervention. Clinical Trial Registration: NCT02588664