Three studies examined the links between attachment insecurity and the use and effectiveness of inducing guilt to produce change in romantic partners (negative‐indirect partner regulation strategies). Individuals higher in attachment anxiety engaged in more negative‐indirect partner regulation strategies (Studies 1–3), but the effectiveness of negative‐indirect strategies depended on targeted partners' attachment avoidance. Targets higher in attachment avoidance reported regulation agents were less successful (Study 1) and reported less motivation to change across time (Study 2) when agents used more negative‐indirect regulation strategies. Negative‐indirect strategies during couples' conflict discussions were also associated with lower problem resolution when targets were higher in avoidance (Study 3). These results provide the first demonstration that target characteristics moderate the effectiveness of negative‐indirect regulation strategies.