In the shift from the “white moderate” of the 1963 Letter from Birmingham Jail to the “white liberal” of the 1967 Where Do We Go from Here: Chaos or Community? Dr. King signaled a critique of (purported) allyship. In the present, political movements on the left are forced to contend with similar questions. Does a problematic ally count as an ally at all? With so much at stake in the present, what, if anything, is worth sacrificing to solidarity? Cutting across decades of art history, this talk examines a series of moments in which the question of problematic allyship has arisen for Black artists and image makers and for scholars who think and write about them (including myself). The particular tools of art history may come into play insofar as this problem intersects with issues of performance, affect, and visibility. But in an age of surveillance and repression, should visibility have limits—and if so, what might these questions teach us about how to do art history?