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Contrary to common beliefs, sometimes downplaying or even undermining one’s case can enhance impact, especially for people with strong attitudes. Across four studies (N = 1,548), we demonstrate that the placement of the undermining information within a two-sided message matters. By manipulating message order within a two-sided message, Study 1 showed that the relative effectiveness of two- over one-sided messages for people with a moral attitude primarily occurred when the two-sided message acknowledged the recipient’s side at the end rather than at the beginning of the message. Studies 2A/B showed that this effect was associated with positive source perceptions, such that placing the acknowledgment at the end results in people with a higher moral basis perceiving the source as more thoughtful and sincere. Furthermore, this inference process was more likely to occur when motivation to think was …