The China–Singapore relationship withstood some major disruptions in 2016, a highly unusual year in the history of the relationship. This article offers a comprehensive examination of China’s changing attitudes towards Singapore as reflected in the wide-ranging reactions across various segments of the Chinese society to the relational tensions in 2016. It reviews the events that disrupted the relationship, identifies seven major areas of disagreement and controversy between China and Singapore, examines the diverse Chinese debates about Singapore, and outlines major challenges for the future of the relationship. Although some of these disruptions in 2016 were incidental and may be explained by tactical misunderstandings and misperception, deeper strategic causes were also at play and may resurface in the future.