The purpose of this transcendental phenomenological study was to develop a composite description of the experiences and instructional decisions of classroom teachers across two low-income public middle schools in New York City, specifically toward homeless students. Using purposeful and criterion sampling to select participants, the study examined the experiences of 12 certified classroom teachers who were aware of students experiencing homelessness. The theories guiding this study were Maslow’s (1970) hierarchy of needs theory and Bronfenbrenner’s (1979) ecological systems theory. Research questions focused on how classroom teachers described their experiences with homeless students and examined their instructional decisions and perceptions of how curriculum serves this group. Data collection methods included preliminary document reviews, personal interviews, written lived experiences, and artifacts. Moustakas’ (1994) reduction methods of analysis were primarily used to interpret collected data to ascertain the essence of participants’ lived experiences. The findings revealed five themes: challenges building trust, academic instructional interventions and considerations, promoting resilience and motivation, socio-emotional impact and support, and curriculum pitfalls and revisions. These findings indicated that teachers serving homeless students navigate through unique personal and professional challenges. Recommendations based on the findings include adopting a more holistic approach to serving homeless students, increased support from school and district administration in these teachers’ pedagogical practices, in-class support staff to mitigate the stressors of serving a high number of homeless students, and giving teachers a say in designing more relevant and equitable curricula for homeless students.