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Returning citizens (formerly incarcerated individuals) face great challenges finding employment, and these are exacerbated by the need for digital literacy in modern job search. Through 23 semi-structured interviews and a pilot digital literacy course with returning citizens in the Greater Detroit area, we explore tactics and needs with respect to job search and digital technology. Returning citizens exhibit great diversity, but overall, we find our participants to have striking gaps in digital literacy upon release, even as they are quickly introduced to smartphones by friends and family. They tend to have employable skills and ability to use offline social networks to find opportunities, but have little understanding of formal job search processes, online or offline. They mostly mirror mainstream use of mobile technology, but they have various reasons to avoid social media. These and other findings lead to recommendations for digital literacy programs for returning citizens.