What are we asking of students when we challenge them to create digital projects from archival or special collections? This paper investigates the rewards reaped and lessons learned from a semester-long course asking students to create a public-facing digital project around an under-researched and underrepresented archive or collection in order to confront issues of power and privilege. The course made use of hands on activities in collections, exposed students to issues of copyright and the postcustodial responsibilities collections have, as well as the biases we can pass along through metadata creation. The practical outcome of this intensive partnership between faculty and librarian was the collection of deliberate approaches to teaching students in special collections, the incorporation of librarian and archivist expertise when partnering with faculty, and the purposeful approach taken when choosing and teaching a digital tool in the humanities.