Counterattitudinal-argument generation is a powerful tool for opening people up to alternative views. Based on decades of research, it seems that this technique should be especially effective when people take the perspective of individuals who hold those views. Yet we find the opposite. In three preregistered experiments (N = 2,734), we find that taking the perspective of someone who endorses a counterattitudinal view lowers receptiveness to that view and reduces attitude change following a counterattitudinal argument generation task. This ironic effect can be understood via value-congruence: Individuals who take the opposition’s perspective generate arguments that are incongruent with their own values, which diminishes receptiveness and attitude change. Thus, trying to “put yourself in their shoes” can ultimately undermine self-persuasion. Consistent with a value-congruence account, this backfire effect is attenuated when people take the perspective of someone who holds the counterattitudinal view yet has similar overall values.