Digital diplomacy is the latest technological advance to push change in diplomatic practice. It relates to the application of digital technologies, including information and communication technologies, software engineering and big data, and artificial intelligence, to the practice of diplomacy. Positioned in the top ranks of connectivity, internet speed, smartphone ownership, and social media usage, South Korea should be a leader in the use of digital technologies in diplomatic practice. However, South Korea is not a leader; indeed, it has been left behind. I explore digital diplomacy as a "disruptive technology" and look at criteria for organizational adaptation. I then use these criteria to assess South Korea's adaptation and draw from these the specific policy challenges facing South Korea. To conclude, I propose four core criteria to aid digital diplomacy adaptation in South Korea and other similar states.