Over the prior decade, structural change efforts have become an important component of community-based HIV prevention initiatives. However, these efforts may not succeed when structural change initiatives encounter political resistance or invoke conflicting values, which may be likely when changes are intended to benefit a stigmatized population. The current study sought to examine the impact of target population stigma on the ability of 13 community coalitions to achieve structural change objectives. Results indicated that coalitions working on behalf of highly stigmatized populations had to abandon objectives more often than did coalitions working for less stigmatized populations because of external opposition to coalition objectives and resultant internal conflict over goals. Those coalitions that were most successful in meeting external challenges used opposition and conflict as transformative occasions by targeting conflicts directly and attempting to neutralize oppositional groups or turn them into strategic allies; less successful coalitions working on behalf of stigmatized groups struggled to determine an appropriate response to opposition. The role of conflict transformation as a success strategy for working on behalf of stigmatized groups is discussed.