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Objective: To identify determinants that contribute to the length of homeless shelter stay. Methods: We utilized a unique dataset from the Homeless Management Information Systems from Boston, Massachusetts, United States, which contains 44,197 shelter stays for 17,070 adults between Jan. 2014 and May 2018. Results: Our statistical analyses and regression model analyses show that factors that contribute to the length of a homeless shelter stay include being female, senior, disability, being Hispanic, or being Asian or Black African. A significant fraction of homeless shelter stays (76%) are experienced by individuals with at least one of three disabilities: physical disability, mental health issues, or substance use disorder. Recidivism also contributes to longer homeless shelter stays. Conclusion: The results suggest possible program and policy implications. Several factors that contribute to longer homeless shelter stay, such as gender, age, disability, race, and ethnicity, may have funding implications. Age may point to the need for early interventions. Disability is developmental and may benefit from treatment and intervention. Finally, we find that length of stay and recidivism are not independent, and may form a vicious cycle that requires additional investigation.