The Homelessness Prevention and Rapid Re-Housing Program (HPRP) provided individuals and families who were either at-risk or currently experiencing homelessness with time-limited financial and housing support services. Evaluations of HPRP showed a high rate of family placement into permanent housing. However, little research has explored immediate and longitudinal outcomes for families enrolled in HPRP. Using Homeless Management Information System data from Indianapolis, Indiana, we examined demographic and program-related predictors of families entering permanent housing and their risk of reentry into homeless services following HPRP participation. The sample included 511 families who enrolled in the program from 2009 to 2012, with an average follow-up period of 4.5 years. We conducted analyses separately for Homelessness Prevention (HP) recipients (n = 357) and Rapid Re-Housing (RRH) recipients (n = 154). Results revealed that HP families were more likely to enter permanent housing if they: included adults who were older in age, were enrolled longer in the program, were provided rental arrear services and utility payments, and did not receive legal services. RRH families receiving rental assistance services had significantly greater odds of entering permanent housing. Among permanently housed families, at least one family member in 10.9% of HP recipients and 18.8% of RRH recipients reentered homeless services. HP families with younger children and one veteran family member were at increased risk of reentry to homelessness services. RRH recipients who did not receive moving cost services and had more children were at greater risk of reentry. Study findings suggest a need for future research on HP and RRH interventions that identify unique service needs among families who are experiencing housing instability or homelessness.