Christianity and culture have had a complex and adversarial relationship since the beginning. Early Christians were counter-cultural—and had an immense impact on the peoples around them. Likewise, medical missionaries have deeply influenced the lives of the peoples where they served over the past two centuries. How? At the same time, they were sensitive to the culture around them, learning language and culture and adapting to religious, social and economic constraints. How have they done this? What does this look like in reality? To answer these questions, I will share survey results and moving stories of medical missionaries serving diverse cultures and religions in culturally intelligent ways in over ten countries on two continents.