With the August 1910 annexation of Korea, the Japanese initiated efforts to redefine their relationship with their new colonial subjects. To this end Seoul’s trilingual media served as an indispensible agency to inform the peninsula’s residents of Japan’s colonial policy and to suggest ways for its development. From the start the Japanese administration clearly advertised its policy as assimilation and used the media to market a new Japanese-Korean relationship to the residents of the peninsula. The messages that appeared in these presses varied and even contradicted each other. Articles carried in the English-language Seoul Press often advertised the Japanese-Korean relationship as amicable and predicted that the two people’s assimilation would be accomplished with relative ease. The Korean-language Maeil sinbo emphasized the changes that Koreans would have to make to attain a level of civilization that qualified them as Japanese imperial subjects. Contrary to the English-language press, it saw assimilation’s success emerging after the people engaged in a long, gradual effort to modernize. Finally, the Japanese-language Keijō shinpō, also aware of the difficulties that historically accompanied assimilation efforts, warned that for assimilation to have a chance at success the Japanese settler would have to adopt a positive image of the Korean people and a cooperative stance toward Japanese administrative efforts. The contradictions found in these messages accented a fundamental problem that Japan’s assimilation policy would face in Korea: the anti-Korean attitudes harbored by Japanese residents in Korea and the discriminative practices evident in Japanese administrative policies neutralized efforts by those Japanese and Koreans who accepted Japan’s colonial rhetoric and strove to advance this new relationship.