This article revisits the issue of the offshore islands in the Taiwan Strait during the Cold War. Benefitting from archival materials only recently made available, specifically Chiang Kai-shek's personal diaries, CIA declassified materials, Taiwanese Foreign Ministry files, and rare publications from the Contemporary Taiwan Collection at the Library of the Institute of Oriental Culture, University of Tokyo, this research examines the cloud of suspicion surrounding the secret contacts between Taipei and Beijing leading up to and during the 1958 offshore islands crisis, elucidating how such a political tête-à-tête, and the resultant tacit consensus over the status of the islands, gradually brought about an end to the conflict between Taiwan and Communist China. In hindsight, the crises over the offshore islands along China's southeast coast momentarily brought the United States closer to war with Communist China, while putting the relationship between Taipei and Washington to a serious test. The end result, however, was that, while these isles were technically embedded in the unfinished civil war between the Chinese Nationalists and Communists, they provided, ironically, an opportunity for secret communications and, ultimately, a kind of détente between the two supposedly deadly enemies across the Taiwan Strait. A close examination of the details of these crises, along with their attendant military, political, and diplomatic complexities, reveals an amazing amount of political intrigue at both the local and international levels that has not been fully realized until now.