Homelessness in America continues to increase yearly, with a recent increase of 2% between 2019 and 2020 (State of Homelessness: 2021 Edition, 2021). Housing insecure individuals often remain unhoused because they experience different barriers and setbacks to their goals of financial and housing stability. While literature has uncovered some of the unique barriers homeless communities face, a majority do not touch on some of the deeper-rooted issues within their communities nor offer solutions for how housing insecure individuals can be supported by the public. For this study, five housing insecure participants were interviewed regarding their difficulties with being homeless, how compassion has shaped their lives, and what goals they have for regaining stability and security in their lives. Two themes emerged from these interviews: barriers to trust and connection and supports for attaining stability and safety. This paper aims to expose the different issues the homeless communities encounter to better understand their hardships and needs. Additionally, this paper offers solutions to encourage support for homeless communities on individual, organizational, and governmental levels.