Does the imperative that we ought to try to understand one another make any sense? Presumably not--"if" it is "correct" that there are indeed different truths, and that the quest for objectivity is appropriate only in certain cultural contexts. After carefully mapping out the epistemological and ethical terrain, with special reference to the notions of "outsider understanding" (and resistance to this idea), "other ways of knowing" and epistemic injustice, this article presents a case for outsider critique. Education for (rational) belief and commitment (to truth and truthfulness) necessarily includes education for understanding. Given our shared humanity, with many overlapping facets that make up our identities, and considering that the standard arguments against outsider "understanding" fail to stand up to critical scrutiny, this arguably also paves the way for the possibility of critical "interrogation" "from the outside". Such interrogation (driven as it may be by a commitment and, indeed, a passion for truth) should display virtues such as sensitivity, patience, perseverance, imagination, empathy and open-mindedness--and should be guided by an honest attempt at understanding.