The relationship between attachment, situational factors (type of esteem threat, target responsibility, and problem severity), and ratings of the helpfulness of esteem support messages was examined in two studies (Study 1, N = 196; Study 2, N = 506). Esteem support is a particular form of emotional support intended to improve how the recipient feels about him or herself. In both studies, participants rated the helpfulness of esteem support messages for three types of esteem threat and completed measures of (a) attachment dimensions, (b) perceived situational severity, and (c) perceived target responsibility. Results indicate that attachment avoidance is related to ratings of message helpfulness and that situational features moderate the relationship between the attachment dimensions and esteem support message ratings.