This article aims to evaluate and assess the health issues of Calgarians over the age of 50 who are experiencing chronic homelessness, determine their unmet service needs, and assess whether there are predictors of chronic homelessness (such as childhood trauma) that could be addressed with changes to policy or service delivery. Three hundred participants were recruited from emergency shelters, as well as a from a small group of rough sleepers in Calgary, Canada in the winter of 2016. Excel and SPSS were used for analysis beginning with descriptive statistics for the samples of respondents who are 50 and older (n = 142) and under the age of 50 (n = 158). More than half of participants had been homeless continually for more than 10 years. Older adults reported complex health issues and significant barriers to accessing health care including finances, wait lists, and asking for help but not receiving it. Older adults reported lower rates of childhood trauma than their younger counterparts, yet the average was two and half times that of the general population. Recognition of the intersecting and cumulative effects of long-term homelessness and age could inform changes to policy to reduce siloes around public systems. Given that older adults are at higher risk for an early death, they should be prioritized for housing programs. Culturally appropriate and trauma-informed interventions are necessary to address the diverse and complex needs of this vulnerable group.