Labor market issues and challenges are primarily understood at an individual level, entrenched socially in policies and initiatives that seek to improve the workplace skills of people having difficulty attaching to the labor market, including people experiencing homelessness. In fact, the labor market is perceived to alleviate a person's situation of homelessness. In 2008 and 2009 qualitative data was collected from 61 employed people experiencing homelessness in Calgary, Alberta, Canada, to better understand the intersection between the labor market and housing-related experiences. Respondents identified aspects of the labor market that were contributing to their current and ongoing situation of homelessness. Implications for practitioners are discussed to help address labor market attachment difficulties experienced by homeless people.