This mixed methods investigation of homeless education in a major urban region identified a number of significant developments and dilemmas amid the larger homeless crisis in the United States. We found that the wider community demographics of homelessness have shifted in recent years, resulting in a higher number of homeless families--many of whom were experiencing homelessness for the first time. In the education domain, these families experienced wide-ranging problems that they perceived as limiters to their advancement. The findings are framed with the help of several elements of Bronfenbrenner's bioecological theory, and several implications for educational leaders are posited. (Contains 7 figures and 6 notes.)