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Whether democracy promotion should play a role in US foreign policy continues to be a subject of considerable debate, perhaps nowhere more than with regard to the Arab World. But looking beyond the "whether," what explains why, where, and how the United States promotes democracy? What caused the shift from the Obama administration's support of the Arab Spring protests in 2011 to its retreat from democracy promotion only two years later? What explains the Trump administration's focus on relationships with autocrats? In the context of these questions, the author explores the tensions between interests and ideals in US foreign policy and the possibilities and limits of US democracy promotion in a region where Washington has often supported autocracy over freedom.