As the global economy and global presence continue to bring visibility, the usefulness of nation branding strategy and digital diplomacy in the cultural approach may help a country ensure success. Taiwan’s Creative Content Agency is the government's latest attempt to increase international relationships and cultural diplomacy between Taiwan and various other countries. This study uses case studies approach to investigate various creative countries, successful and unsuccessful, to provide a qualitative measurement of theme and problem-solving. This study also conducted in-depth interviews to examine the existing policy and the implementation of strategies by the Creative Content Agency to increase positive perception of Taiwan’s nation brand and cultural products within a global stage. This study offers suggestions for improvement, potential areas of caution, and analysis of changes in paradigm or current policies that have shown success in other creative countries’ contexts via creative nation branding theory.