Digitalization is exposing developing countries to a growing number of risks, as well as opportunities associated with connecting to the Internet. Myanmar stands out as a critical case of both the pitfalls and the benefits Internet connection can bring. Amidst a political transition from military rule to a functioning democracy Myanmar is adding ICT to key areas like banking and e-government. Having been one of the least connected countries in the world only five years ago the country is now connecting to the Internet at an unprecedented pace, with little or no institutions in place to ensure the transition goes smoothly. Using the framework of Cyber Security Capacity Building (CCB) we examine the risks and potential benefits of Myanmar’s embracement of digital technologies.