The authors present and test a model of interpersonal insecurity compensation. According to this model, perceivers detect targets' chronic insecurities about interpersonal acceptance, become vigilant about upsetting targets, and respond with affective exaggeration, which involves cautiously inflating positive thoughts and feelings about targets and concealing negative sentiments. Results of 3 studies support this model across a variety of relationship types. Perceivers who detected targets' chronic insecurities concealed negative sentiments when they believed their sentiments would be observed by targets (Study 1), converged with other perceivers in their self-reported affective exaggeration to insecure targets (Study 2), and reported vigilance about upsetting targets, which predicted perceivers' enhanced cognitive processing of targets' daily insecurity and intensified their tendencies to exaggerate affections in response to that insecurity (Study 3). Perceivers' affective exaggeration appeared to enhance chronically insecure targets' perceptions of being valued by perceivers, but it also predicted perceivers' reduced relationship satisfaction (Studies 2 and 3). Results underscore the active, but perhaps dissatisfying, regulation of relationships with chronically insecure relationship partners.