Prevention programs yield modest reductions in bullying in North American schools. This study explored the perspective of educators regarding factors limiting the impact of these initiatives. Transcripts from nineteen 90-min focus groups with 103 educators were coded thematically. Educators felt that off-site incidents, cyberbullying, and the growing involvement of boys in psychologically aggressive incidents have increased the complexity of bullying. Curriculum demands limit time for training, implementation, and prompt responses to bullying. Principals failing to back teachers up, ambivalent colleagues, uncooperative parents, and a lack of evidence reduce their commitment to implementation. Promising programs are discontinued in favor of new initiatives. Some educators modified programs; others, feeling frustrated and discouraged, struggled to mobilize the enthusiasm needed to ensure successful implementation. Dealing with bullying in the face of limited time, training, and support may increase emotional exhaustion and compromise program effectiveness.