A 2016 report by the San Diego County Grand Jury found that the East County cities of El Cajon, La Mesa, Santee, and Lemon Grove lacked an adequate response to addressing homelessness (San Diego County Grand Jury, 2016). Lemon Grove had the smallest overall population among the four cities referenced in the report, as well as the smallest unsheltered homeless population (Regional Task Force on the Homeless, 2015). Publication of the grand jury’s report garnered media attention and public interest, leading to the city’s partnership with the Sage Project at San Diego State University to explore strategies to address homelessness (Pearlman, 2016). This study incorporates qualitative research of primary and secondary source data from county, regional, state, and federal public records, direct communication with stakeholders, site visits, and peer-reviewed literature from political science, public health, sociology, organizational behavior, and public relations to examine the existing framework addressing homelessness and provide recommendations for small to medium-sized cities in San Diego County, like Lemon Grove, to connect with available resources and deliver them to their homeless residents through membership and participation in the Regional Task Force on the Homeless. This report explores four main research questions in order to develop recommendations to Lemon Grove city leadership based on their inputs to Sage Project participants, as well as additional documentation they provided from other studies undertaken to support the city’s General Plan Update in 2017. The results of scholarship yield two key recommendations for city leaders. First, it is recommended that the Lemon Grove City Council make homelessness a top priority in the agenda it provides to the city manager and staff to execute. Second, it is recommended that Lemon Grove join and take an active, participatory role in the San Diego Regional Task Force on the Homeless.