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Existing scholarship on irregular regime transitions is siloed, exploring the causes and consequences of coups, uprisings, and interventions in isolation of the others. This article introduces a theoretical framework that ties these various types of transitions together. It does this by investigating how the size of the coalition that brings a leader to power --- the transitional coalition --- combined with the presence or absence of outside influence affects the prospects for democratization. Irregular transitions involving large transitional coalitions are the most likely to result in democratic gains. The opposite is true for transitions with small coalitions. External influence can be a mixed blessing, exerting a democratizing effect in some contexts and an autocratic effect in others. Analyzing the universe of successful irregular regime transitions since 1955, we find strong support for our theoretical claims. These findings advance understanding of the major drivers and inhibitors of democratization following irregular transitions.