Librarians face numerous challenges when helping patrons—particularly those with low socioeconomic status (SES)—meet information needs. They are often expected to have knowledge about many different technologies, web services, and online forms. They must also navigate how to best help patrons while ensuring that personally identifying information (PII) is kept private and that their help will not hold them or their library system liable. In this paper, we explore data collected in eleven focus groups with 36 public librarians from across the U.S. to understand the information challenges librarians encounter when working with patrons who have low digital literacy skills but must increasingly use the internet to request government assistance, apply for jobs, and pay their bills. Findings highlight the thin line librarians must walk to balance issues around privacy, trust, and liability. We conclude the paper with recommendations for libraries to provide additional training to librarians and patrons on privacy and information technology, and we suggest ways for librarians to fulfill their roles as information intermediaries while minimizing legal, ethical, and privacy concerns.