Beginning in 2007, a community health center and a community health worker organization collaborated on a community health worker initiative to improve diabetes outcomes among underserved communities. Despite a shared vision, the initiative ended prematurely because of a number of unexpected collaborative challenges. This article describes the results of a qualitative investigation into these challenges. Through examples, we show how our collaborative difficulties were due to 3 interacting influences: logistics, participation, and institutional culture. We argue for the importance of institutional cultural competency in health care collaborations and provide recommendations for future collaborations that takes into account these 3 overarching influences.