Diplomatic manipulation and wars were the two main tools that were used in dealing with political problems between two countries during the disunited period of the Three Kingdoms. The former was used to negotiate the conflict between kingdoms and the breakout of war was a symbol of diplomatic failure. During the earlier years of the Three Kingdoms, the priority for each kingdom was to ensure the complete control of its territories as well as to strengthen its internal construction and consolidation. Therefore, peace keeping was necessary and expected as well. Under these considerations, diplomacy was far more important than war. Generally speaking, for each kingdom there was a close relationship between the development of diplomatic policy and its internal stability. For example, Tsao Tsao and his son Tsao Pe had the control of the most fertile lands and bounteous resources among the Three Kingdoms. This advantageous position provided Tsao Wei with a higher hand in handling diplomatic policy with its rivalries. With solid backup behind them, Tsao Wei would go to war instead of seeking diplomatic solutions. On the other hand, without the abundant resources in land, population, and political power as Tsao Wei, Wu and Shu had to form an alliance to oppose Tsao Wei. However, this alliance, which was formed as a result of political gain and practicality, could change quickly whenever Tsao Wei lost its power or Wu and Shu gained strength. Whether the purpose was routine or goal-oriented diplomacy, the chosen diplomat would strive for the best interest of the country. Especailly during the period of disunity, most diplomats would face and deal with dangerous and difficult situations. Therefore, the diplomats during that period were very witty, talented, and literary gifted. Since the Battle of the Red Cliffs, the power struggle among Wei, Su, and Wu provided many skillful envoys with the opportunity to seek various allegiances among the Three Kingdoms. The purpose of this paper is, through the detailed research of the historical documents in diplomacy of the Three Kingdoms, to analyze the diplomatic background of the Three Kingdoms and to reveal the mission of the diplomats as well as the characteristics of choosing the proper envoys for the job.