Abstract: In recent years, the number of individuals experiencing homelessness has increased in the United States. This paper analyzes 2019 data from 16 different emergency shelters in Monroe County, located in Upstate New York. The data were collected through the County’s Homeless Management Information System (HMIS), and individuals were de-identified and de-duplicated for analysis. The purpose of this study is to explore the basic characteristics of the homeless population in Monroe County, and the dynamics of shelter use. The results of this study showed gender as a significant factor when analyzing the relationship between demographic variables and recorded reasons for shelter entry. Results also indicated that age and ethnicity did not significantly influence odds of re-entering a shelter, but did significantly influence reasons for shelter entry. Overall, the most common recorded cause of shelter entry in 2019 in the examined county was eviction by primary tenant. Recommendations to better address recurrent shelter entry and potential chronic homelessness include more consideration for the diversity existing within the homeless population, and the dynamics leading to shelter stays, including enhanced funding and training for shelter staff, as well as expanded access to permanent supportive housing programs.