During the first Japanese invasion of Korea, Japanese forces led by Toyotomi Hideyoshi captured Pyongyang, although they were ultimately unable to hold it.

Toyotomi Hideyoshi ( , 17 March 1537 18 September 1598) born Kinoshita Tkichir, later called Hashiba Hideyoshi, was a Japanese samurai and daimyo (feudal lord) of the late Sengoku period regarded as the second "Great Unifier" of Japan.Hideyoshi rose from a peasant background as a retainer of the prominent lord Oda Nobunaga to become one of the most powerful men in Japan. Hideyoshi succeeded Nobunaga after the Honn-ji Incident in 1582 and continued Nobunaga's campaign to unite Japan that led to the closing of the Sengoku period. Hideyoshi became the de facto leader of Japan and acquired the prestigious positions of Chancellor of the Realm and Imperial Regent by the mid-1580s. Hideyoshi launched the Japanese invasions of Korea in 1592 to initial success, but eventual military stalemate damaged his prestige before his death in 1598. Hideyoshi's young son and successor Toyotomi Hideyori was displaced by Tokugawa Ieyasu at the Battle of Sekigahara in 1600 which would lead to the founding of the Tokugawa Shogunate.

Hideyoshi's rule covers most of the AzuchiMomoyama period of Japan, partially named after his castle, Momoyama Castle. Hideyoshi left an influential and lasting legacy in Japan, including Osaka Castle, the Tokugawa class system, the restriction on the possession of weapons to the samurai, and the construction and restoration of many temples, some of which are still visible in Kyoto.

The Japanese invasions of Korea of 1592–1598 or Imjin War involved two separate yet linked invasions: an initial invasion in 1592 (Imjin Disturbance), a brief truce in 1596, and a second invasion in 1597 (Chongyu War). The conflict ended in 1598 with the withdrawal of Japanese forces from the Korean Peninsula after a military stalemate in Korea's southern provinces.The invasions were launched by Toyotomi Hideyoshi with the intent of conquering the Korean Peninsula and China, which were respectively ruled by the Joseon and Ming dynasties. Japan quickly succeeded in occupying large portions of the Korean Peninsula, but the contribution of reinforcements by the Ming, as well as the disruption of Japanese supply fleets along the western and southern coasts by the Joseon navy, (commanded by Yi Sun-sin) forced a withdrawal of Japanese forces from Pyongyang and the northern provinces to the south in Busan and nearby regions. Afterwards, with righteous armies (Joseon civilian militias) launching guerrilla warfare against the Japanese and supply difficulties hampering both sides, neither were able to mount a successful offensive or gain any additional territory, resulting in a military stalemate. The first phase of the invasion lasted from 1592 until 1596, and was followed by ultimately unsuccessful peace negotiations between Japan and the Ming between 1596 and 1597.

In 1597, Japan renewed its offensive by invading Korea a second time. The pattern of the second invasion largely mirrored that of the first. The Japanese had initial successes on land, capturing several cities and fortresses, only to be halted and forced to withdraw to the southern coastal regions of the peninsula. However, the pursuing Ming and Joseon forces were unable to dislodge the Japanese from their remaining fortresses and entrenched positions in the southern coastal areas, where both sides again became locked in a ten-month long military stalemate.

With Toyotomi Hideyoshi's death in 1598, limited progress on land, and continued disruption of supply lines by the Joseon navy, Japanese forces in Korea were ordered to withdraw back to Japan by the new governing Council of Five Elders. Final peace negotiations between the parties followed afterwards and continued for several years, ultimately resulting in the normalization of relations.