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Under what conditions can leaders remove constraints on their power without facing sanctions from regime elites? We analyze an infinite-horizon bargaining model between a leader and his ruling coalition. The leader can offer sticky power-sharing arrangements, but occasionally has the opportunity to roll back these deals---autocratization. Weak leaders who infrequently have the opportunity for autocratization face the greatest incentives to capitalize on their rare opportunities to roll back institutional constraints. Counterintuitively, strong leaders are more likely to keep power-sharing arrangements in place because they are more frequently able to remove these constraints. Autocratization does not necessarily trigger fighting by elites even though the ruling coalition has full information about the leader’s actions. We test our theoretical findings using an original global dataset of term limits and cabinet appointments in all countries (dictatorships and democracies) from 1960 to 2020.