Survival sex is associated with many health problems, including increased substance use and HIV risk. Current research on survival sex among homeless individuals has given little attention to the unique effects of how length and number of homeless episodes influence engagement in survival sex. Using secondary data analysis from the Washington, DC, Metropolitan Area Drug Study (DC*MADS) (N = 783), the authors examined the relationship of days and number of times homeless to engagement in survival sex, while controlling for other sociodemographic and clinical characteristics. Results showed that length of homelessness and number of homeless episodes, as well as current age, previous drug use, depression, and institutionalization, increased the odds of engaging in survival sex. Results support current efforts on interventions to transition homeless individuals into housing as rapidly as possible. Service providers assisting the homeless can affect engagement in survival sex and its associated risks through creating referral networks for integrated treatment programs for co-occurring substance use and mental health problems while advocating for early housing interventions and increased housing retention. Further research is needed regarding the ways in which length of homeless episodes affects risky behaviors such as survival sex, with a particular focus on all age groups.