In 2017, Dapiran published his first book "City of Protest: A Recent History of Dissent in Hong Kong" with Penguin Books, which dealt with the history of protest movements in Hong Kong since the 1960s. In the book, Dapiran particularly focuses on the 2014 Hong Kong Protests. According to Dapiran, witnessing these protests made him "realise my identity as a Hongkonger." Since the publication of Dapiran's first book, he has become one of the leading Western commentators on Hong Kong protest movements, in particular during the 2019-2020 Hong Kong Protests. He has been praised in the "South China Morning Post" as being "renowned as a clear-eyed observer of the city’s politics" and is often quoted as an expert on Hong Kong by media such as "Quartz", the "Financial Times" or "Time""." Writing in publications such as "The Guardian", "The Atlantic", "New Statesman, CNN" and "Foreign Policy" and appearing on programs like the BBC, Bloomberg TV, Reuters, RTHK and ABC, Dapiran has been highly critical of the Hong Kong government and the Chinese central government in Beijing, asserting, for example, that "the Hong Kong government is no longer acting in the best interests of its people," that "Beijing has taken advantage of global distraction [due to the outbreak of Covid-19] to begin taking retribution for Hong Kong’s open defiance of China’s rule" in 2019, and that the Chinese government uses the law to act against the opposition in Hong Kong. In July 2020, he claimed that the Chinese government is acting like a "colonial power" in Hong Kong and that "the U.S. measures, alongside Beijing’s own crackdown on Hong Kong, are fast turning the city from an open, stable international financial center to contested ground at the very front lines of a rapidly intensifying geopolitical conflict." Since 2020, he also writes a regular column for the Hong Kong Outlet Citizen News.