Few interventions train homeless consumers in housing-related independent living skills. To inform the development of such interventions for the Department of Veterans Affairs' Supported Housing consumers with serious mental illness, we examined these consumers' problem-solving skills and deficits. We performed semistructured interviews and cognitive tests with 20 consumers who retained housing for ≥1 year ("stayers") and 20 consumers who lost housing in <1 year ("exiters"). Salient types of problems were identified in the qualitative data; we categorized problem-solving approaches by complexity level and identified differences in problem-solving complexity by consumers' housing outcomes. Instrumental (e.g., money management), interpersonal, and health-related problems were prominent in consumers' narratives. Cognition was poor among stayers and exiters. Problem-solving approaches were highly relevant to day-to-day functioning in supported housing. There was a trend toward greater problem-solving complexity in stayers versus exiters. These data explore potential challenges faced in supported housing and help inform the development of a Veterans Affairs-based housing-focused skills training intervention. (PsycINFO Database Record (c) 2019 APA, all rights reserved).