Abstract: On June 12, 2018, U.S. President Donald Trump and Democratic People’s Republic of Korea (hereafter DPRK or North Korea) leader Kim Jong Un, Chairman of the State Affairs Commission, met in Singapore for the first time. The two men signed a joint declaration and pledged to work toward denuclearizing the Korean Peninsula and improving bilateral relations. These developments raise several questions. What impact will this summit meeting between the two leaders have on regional security? What sorts of opportunities and risks will that impact produce for Japan? How should Japan deal with this fluid regional situation?