Objectives: The U.S. Department of Veterans Affairs (VA) is transitioning to a Housing First approach to placement of veterans in permanent supportive housing through the use of rental vouchers, an ambitious organizational transformation. This qualitative study examined the experiences of eight VA facilities undertaking this endeavor in 2012. Methods: A multidisciplinary team interviewed facility leadership, midlevel managers, and frontline staff (N=95 individuals) at eight VA facilities representing four U.S. regions. The team used a semistructured interview protocol and the constant comparative method to explore how individuals throughout the organizations experienced and responded to the challenges of transitioning to a Housing First approach. Results: Frontline staff faced challenges in rapidly housing homeless veterans because of difficult rental markets, the need to coordinate with local public housing authorities, and a lack of available funds formove-in costs. Staff sought to balance their time spent on housing activities with intensive case management of highly vulnerable veterans. Finding lowdemand sheltering options (that is, no expectations regarding sobriety or treatment participation, as in the Housing First model) for veterans waiting for housing presented a significant challenge to implementation of Housing First. Facility leadership supported Housing First implementation through resource allocation, performance monitoring, and reliance on midlevel managers to understand and meet the challenges of implementation. Conclusions: The findings highlight the considerable practical challenges and innovative solutions arising from a large-scale effort to implement Housing First, with particular attention to the experiences of individuals at all levels within an organization.