The current study examined the relationship between risk factors for prisoner self-injurious behavior (SIB) and the amount of time male prisoners function without engaging in SIB (SIB-free time), and obtained estimates of SIB-free time for selected SIB prisoner subgroups dependent on their housing status. Conditional Cox regression analysis revealed that a risk model consisting of developmental, mental health/health, legal/offense, and institutional functioning factors accounted for 56% of the difference in risk between SIB (n = 132) and non-SIB male prisoners (n = 132) who were matched according to security level and conviction prefix, estimating a SIB risk probability of less than or equal to 0.50 at greater than or equal to 36 months of SIB-free time. Survival analyses revealed that administrative segregation placement drastically reduced SIB-free periods for certain SIB prisoner subgroups. Some potential practice implications for correctional mental health and security/classification professionals and directions for future research are discussed. (Contains 4 tables.)