School social workers are at the forefront of serving homeless children and youths as they pursue education. Because of the negative impact homelessness can have on academic outcomes for children, understanding what factors are perceived to either hinder or facilitate practice and what factors might influence perceptions of practice with this population is important, but understudied. The purpose of this study was to examine what aspects of school social work are perceived to serve as barriers and which are seen as facilitators to working with homeless children, how those aspects may be categorized, and what might influence perceptions of these barriers and facilitators. A sample of 228 school social workers was surveyed regarding their perceptions of 15 different aspects of practice with homeless children. It was established that all 15 aspects were viewed as barriers, grouped into two types: general homeless barriers and in-school barriers. Awareness of homelessness was found to correlate with perceptions of barriers, and level of licensure and geographic location moderated that relationship. Findings from this study indicate that school social workers must be cognizant of the issues in their service area and the barriers that may hinder practice with homeless children in a school setting.