The community colleges are fertile ground for ongoing efforts to democratize digital humanities, but infrastructural challenges and concerns about digital surveillance pose unique problems for instructors pursuing digital pedagogy in the community college classroom. This is particularly true at campuses that serve economically disadvantaged students with limited access to computers and unreliable internet connections at home. Students from historically underrepresented groups, who make up the bulk of community college students in my region, also face challenges in completing digital projects, including apprehensions about maintaining a public digital footprint due to immigration status. This poster presentation explores how the digital divide, specific concerns of underrepresented students, and technology infrastructure limitations on campus have shaped my attempts at digital pedagogy at a leading community college in the Los Angeles area.