Abstract This article discusses the contours of U.S. diplomacy in Czechoslovakia before and during the Velvet Revolution of 1989, showing how the U.S. embassy in Prague, in collaboration with the U.S. National Security Council (NSC) and State Department, crafted U.S. policy. Drawing on recently available primary materials (including declassified U.S. telegrams, Czechoslovak archival documents, unpublished memoirs, and original interviews), this article highlights the role of the U.S. embassy during the period from August to November 1989, including how key officials, above all Ambassador Shirley Temple Black, analyzed political developments, assisted Czechoslovak dissidents, and pursued extensive engagement with the Communist government. The article provides the first scholarly, granular account of U.S. diplomacy in Czechoslovakia during the November 1989 upheavals and contributes to the historiography on U.S. foreign policy and the end of the Cold War.