Homelessness is a social issue that is starting to be addressed not only by private or non-profit organizations, but also by local law enforcement agencies. This process evaluation was conducted through observations and interviews of the Chula Vista Police Department Homeless Outreach Team. A small team that is taking on the challenge of addressing the city’s issues related to homelessness and seek to improve the lives of the individuals living in homelessness. This team’s mission is to find housing solutions for the unhoused and offer services in partnership with other organizations. Interviews and ride-along observations with the team’s sergeant, two officers, and park ranger revealed how the Chula Vista Police Department Homeless Outreach Team view homelessness, and individuals living in homelessness through a variation of systems theory. They focus on addressing the root cause of a person’s homelessness and not only treating the symptoms. This evaluation gives insight into their outreach practices, their efforts to find simple solutions, and their understanding of their role as an officer versus their role as a social worker. Using this information, the team can continue to develop their strategy to create partnerships in areas where clients lack services and better engage the community through community and active participation in the work that they are accomplishing. Keywords: homelessness, law enforcement, process evaluation, outreach practices