This article draws upon two conceptual frameworks--institutional culture in education and innovation studies--to contextualize findings from a digital intervention for underrepresented students applying to college. The qualitative data that inform this study's findings include 88 open-response surveys with school teachers, as well as campus observations from 52 participating high schools in the U.S. state of California. Through such a conceptual framework, this article highlights four institutional barriers that can inhibit widespread adoption of a promising innovation: (a) the challenge of tapping into participants' intrinsic motivation; (b) forging opportunities for collaboration and communication between different stakeholders; (c) finding adequate time to schedule and implement an innovation; and (d) a dearth of support for digital resources.