Since constitutional government began in 2011, Myanmar’s shift from an entrenched military regime has drawn wide interest from policy analysts. This article explores the context of Myanmar’s fragile democratisation from the ground up. It explains two interlocking characteristics: the fundamentally novel character of reform and the endurance of age-old conundrums. For longer term success, ensuring that Myanmar has adequate capacity—at institutional and human levels—to manage its turbulent transformation will not be easy or cheap. This will also require a move away from stale rhetoric about non-disintegration, national solidarity and the perpetuation of sovereignty. The next step is to develop a culture of adherence to free and fair elections, followed by a wide-ranging democratisation of how post-dictatorship politics is conceived.