The Housing Choice Voucher (HCV) program, which is the largest rental subsidy program in the United States, relies on the participation of landlords. Research shows, however, that not all landlords are willing to participate. The present study analyzes qualitative, semi-structured interviews conducted with landlords (N = 25) in an effort to deepen our understanding of their experiences with the HCV program, and specifically, to explore the challenges they face in communicating with the public housing authority (PHA). The sample comes from a city where the financial incentive to participate is not strong, and a lack of source of income protections makes landlord participation more voluntary. Landlords reported communication issues with the local PHA as one of the biggest challenges of working with the program—specifically, difficulty interacting with staff and accessing program information. Ultimately, these communication issues created negative experiences for landlords, characterized by frustration and feeling unsupported, which led some to reduce their participation. These findings suggest a need to improve communication between PHAs and currently participating landlords, especially in light of recent expansions in the HCV program.