Individuals who experience mental illness and substance abuse are at serious risk for homelessness. Researchers have not demonstrated how face-to-face contacts between dually diagnosed homeless individuals and case managers can impact the participants' length of stay in transitional housing programs. The purpose of this archival, exploratory study was to determine if increases in face-to-face contacts between dually diagnosed homeless participants and case managers can shorten the length of stay in transitional housing programs. The impact of different staffing types (on-site staffing and community-based staffing) within housing programs on length of stay was also examined. The psychotherapeutic theory of the therapeutic alliance served as the theoretical underpinning for this study. The sample included 227 dually diagnosed homeless men and women from 3 transitional housing programs. The data for this study were collected over a 5-year period of admission and discharge forms. Data were analyzed using correlations and regression analyses. Results revealed that an increase in face-to-face contacts with case managers predicted shorter length of stay in transitional housing for dually diagnosed participants. Additional significant relationships between age, gender, diagnoses, face-to-face contacts, length of stay, and program outcome were found. Findings from this study inform social change by demonstrating that community based programs are effective in working with homeless participants. Transitional housing programs can enhance the effectiveness of their services by training staff to interact face to face with the participants earlier in the program, thus establishing therapeutic alliances sooner.