A tire inflation valve having anti-rotation features has an external valve seat, and includes a valve body, a valve stem extending through the length of the valve body, and anti-rotation features disposed interior to the valve body. The valve stem is configured to move relative to the valve body, such that a resilient seating surface disposed at a proximal end of the valve stem is displaced relative to a valve seat formed by an exterior surface of a proximal end of the valve body. The anti-rotation features may include a complementary slot and protrusion, a keyway and complementary protruding ridge, and/or complementary channels and lateral protrusions.