Since June 2013, the Afghan National Security Forces (ANSF) have taken over major responsibility for Afghanistan’s security throughout the country. Recently, during the two rounds of the presidential elections they have proved capable of defending territory and preventing major attacks, a fact that has been widely seen as evidence of their progress. After the relatively peaceful 14th June runoff, many observers expressed confidence that Afghan army and police are sufficiently strong to hold off any relevant military challenge by the Taliban and other Armed Opposition Groups (AOG). Although their recent performances exceeded expectations, ANSF’s readiness to confront autonomously the challenges posed by insurgency and the ability to rely on their own capacity remains dubious. ANSF still face a complex set of challenges that derive from the economic, security, political transitions undergoing in Afghanistan. This study discuss the interrelated challenges to transitioning Afghan-led security by the end of 2014, the date that would mark the transfer of all combat responsibilities to Afghan government forces. A special focus is dedicated to the Afghan National Army (ANA), as it is commonly considered the most advanced element of the ANSF.