As children enter preschool and subsequently transition to kindergarten, they are increasingly confronted with the social challenge of initiating and maintaining relationships with unfamiliar peers. Indeed, it is in the peer context that the costs of toddler BI seem most apparent as BI begins to manifest behaviorally as social reticence (Rubin et al. 2009). Especially problematic is that, for children high in BI, withdrawal and reticence can be negatively reinforcing in that they allow children to avoid sources of anxiety (i.e., novel settings and peers), while limiting opportunities to learn that feelings of anxiety may be unfounded or, at the very least, manageable. As displays of social withdrawal become increasingly ingrained, peers begin to recognize such behaviors as aberrant (Ladd 2006) resulting in peer exclusion, rejection, and victimization, even in early childhood (Gazelle and Ladd 2003; Nelson et al. 2005). Being rejected can ultimately lead to a maladaptive cascade that, if left unchecked, may result in reduced displays of socially competent behaviors, elevated social anxiety, increased loneliness, lower self-esteem, and higher levels of depression (Rubin et al. 2009). Despite the importance of BI to children’s social functioning, few researchers have examined whether existing treatments for young children with elevated BI and/or anxiety generalize to relevant social contexts, which is the primary aim of the present pilot study.