Formerly incarcerated individuals face a number of obstacles transitioning home, among which job search is one of the critical issues. While searching for a job can be difficult for most people, returning citizens face additional obstacles due to their criminal records, gaps in employment, and reduced professional networks. Furthermore, returning citizens often have been incarcerated in prisons with little to no internet access. With this in mind, job search challenges are compounded by the fact that digital literacy is increasingly required to address them. Job search involves several digital elements, including searching for job postings, preparing an online resume, applying online, and communicating via email. Despite a considerable body of literature on the difficulties of reentry, there is limited research addressing the interaction between digital literacy and job search for returning citizens and little scholarly effort to design digital literacy programs for them. Drawing on semi-structured interviews, action research in the classroom, and a design studio workshop, this dissertation explores the following research questions: (1) How do returning citizens interact with digital technologies, both in general and specifically for job search? (2) What challenges do returning citizens have as they seek to gain digital literacy skills? (3) How can digital technology be better designed to support returning citizens and their social support in digital literacy skill development for job search?Through my research, I found that social support members play a pivotal role in helping returning citizens learn digital literacy skills and obtain access to a mobile phone. While returning citizens mirror mainstream populations in their mobile phone usage, they are wary of social media and face significant challenges distinguishing good and bad content online. Returning citizens also face substantial challenges determining when and how to disclose their criminal past on online applications. However, when faced with concerns about employment discrimination, especially racism, participants maintained a practical outlook.Based on these findings, I recommend including social support members in the design of digital literacy for job search tools. I emphasize creating practical and applied digital literacy for job search course content that addresses the unique experiences of this population. Finally, I recommend the design of digital literacy for job search tools that reduce redundancy and engage users beyond text entry and text-based content.My empirical research contributes to improved knowledge of how this population fares outside of prison, specifically as it relates to job search and digital literacy. I suggest new features in curriculum design and the design of tools and resources for digital literacy for job search, specifically as it relates to returning citizens and their social support networks. Lastly, this dissertation also highlights the sub-context of the challenges of race, racism, and employment discrimination as it relates to the formerly incarcerated community navigating the digital aspects of job search. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]