Because of the close ties between Chosun and China, almost Chosun kings set great store by Chinese language teaching and the cultivation of talents in the language. Some of the kings themselves were fluent speakers of Chinese, and tried to make their sons acquire the same ability. A few even took part in the official assessment of their ministers’ abilities in the language. Chinese learning institutes were established; and Chinese learning manuals, complied in large quantity. Yet despite their efforts, the results were sadly disappointing, at least to most of the kings, who lamented constantly of the low language standards. This paper is an exploration of the causes of the failure of the imperial efforts. Based largely on the Chosun Imperial Records, it examines the Chinese language teaching under the imperial auspices (with special focus on speech training), the measures upholding the prestige of Chinese learning, and the ultimate failure. It is hoped that by learning from the past, we can find directions to improve the Chinese teaching of today.