Coalitions provide the potential for merging the power, influence, and resources of fragmented individuals and institutions into one collective group that can more effectively focus its efforts on a specific community health issue. Connect to Protect® coalitions devote resources to address the HIV epidemic at a structural level. This study examines differential challenges in coalition processes that may hinder coalition building to achieve HIV prevention through structural change. Qualitative interviews conducted with community partners participating across 10 coalitions were analyzed to compare responses of those individuals working on HIV prevention coalitions targeting adolescent and young adult gay and bisexual men versus those targeting adolescent and young adult heterosexual women. Community partner responses revealed differences across several key areas including: (a) acceptability and goals in discussing sexual issues with adolescents, (b) goals of sexual health promotion activities, and (c) competition among collaborating agencies. Themes highlighted in this study can complement existing community intervention literature by helping community mobilizers, interventionists, and researchers understand how cultural norms affect youth-specific coalition work.