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Despite recognizing the important role that opposition parties can play in processes of democratization, international democracy promotion practitioners working in non-democracies are often hesitant to engage too directly with opposition politicians. Some of this hesitance derives from legal restrictions and bureaucratic concerns, which have “tamed” democracy promotion over time. But another set of challenges also hampers collaboration: the difficulty of identifying promising parties that are genuinely committed to reform and democracy. In this paper, I outline the dual challenges that plague interactions between democracy promoters and opposition parties—what I call the dilemma of electoral viability and the dilemma of democratic credibility—and how these impact relations between these sets of actors in autocratic contexts. Relying on elite interviews with opposition politicians and democracy promotion practitioners, as well as in-depth historical case analysis, I show how these challenges can discourage democracy promoters from partnering with opposition politicians, which can undermine their capacity to promote democratic change, particularly in an era of autocratization. I further suggest that when opposition parties are able to credibly signal their domestic popularity and commitment to democratic norms, they are more likely to overcome the twin dilemmas and achieve fruitful working relationships.