Ukraine has faced substantial challenges across multiple fronts its successful 2014 Revolution of Dignity. Among the greatest challenges Ukraine has faced is the establishment of a national cybersecurity infrastructure capable of withstanding cyberattacks and information operations against military and civilian infrastructures. Ukraine’s experience is counterintuitive to the constant refrain in cyberspace regarding asymmetric advantage. Ukraine has struggled with the help of European and NATO allies to forge multiple organizational structures capable to facilitating national cyber defense. This work offers detailed analysis on the construction of national cyber capabilities by a medium sized state under duress and coercion from an adversary state by leveraging interviews with and documents from Ukrainian ministers, General Staffs, Security Service personnel, soldiers, journalists, civilians and academics conducted over two years. The result is analysis that informs the underlying notions about small to medium state cyber defenses in relation to well-resourced adversaries.