Recent studies based on attachment theory demonstrate that dispositional and experimentally manipulated attachment security facilitate cognitive openness and empathy, strengthen self-transcendent values, and foster tolerance of out-group members, suggesting an effect of one behavioral system, attachment, on another, caregiving. Here we report 2 studies conducted in 3 different countries (Israel, the Netherlands, and the United States) to determine whether the 2 dimensions of attachment insecurity—anxiety and avoidance—are related to real-world altruistic volunteering. In both studies and across the 3 locations, avoidant attachment was related to volunteering less and having less altruistic and exploration-oriented motives for volunteering. Anxious attachment was related to self-enhancing motives for volunteering. Additional results suggested that volunteering ameliorates the interpersonal problems of individuals high in anxiety and that volunteering has more beneficial effects if it is done for altruistic reasons. Future directions for experimental research on this topic are outlined.