It can be challenging for support providers to facilitate effective social support interactions even when they have the best intentions. In the current article, we examine some reasons for this difficulty, with a focus on support recipients’ self-esteem as a crucial variable. We predicted that recipients’ receptiveness to support would be influenced by both support strategy and recipient self-esteem and that receptiveness in turn would impact providers’ perceived caregiving efficacy and relationship quality. Study 1 (hypothetical scenarios), Study 2 (confederate interaction), and Study 3 (reports of recently received support) showed that individuals with low self-esteem (LSEs) are less receptive than are individuals with high self-esteem (HSEs) to support that positively reframes their experience but are equally receptive to support that validates their negative feelings. In Study 4, providers demonstrated some knowledge that positive reframing would be less helpful to LSEs than to HSEs but indicated equal intention to give such support. Study 5 showed that, in a real interaction, friends were indeed equally likely to offer positive reframing to both LSEs and HSEs but were less likely to offer validation to LSEs. LSEs were less accepting of such support, and in turn providers felt worse about the interaction, about themselves, and about their friendship more broadly. Study 6 confirmed that recipients’ receptivity to support directly influenced providers’ experience of a support interaction as well as their self- and relationship evaluations. The findings illustrate how well-meaning support attempts that do not match recipients’ particular preferences may be detrimental to both members of the dyad.