On entering the White House, US President Barack Obama aimed to put the war in Afghanistan at the forefront of his security agenda following eight years of neglect by a Bush administration preoccupied by the war in Iraq. The Obama administration spent nearly a year reviewing the situation in Afghanistan and vetting war options amid protracted interagency deliberation and partisan debate. By the end of 2009, President Obama affirmed his administration’s commitment to degrading the capabilities of terrorist groups ensconced in Afghanistan and Pakistan and announced that, by the end of July 2011, the US would begin a conditions-based transfer of responsibility to the Afghan government and security forces, enabling the United States to diminish its kinetic military activities in favour of a more “typical” presence with Washington continuing to providing development and economic assistance, plus training for military and civilian personnel. Thus the counter-insurgency mantra of “clear, hold and build” became, under Obama, “clear, hold, build and transfer.” This paper evaluates the viability of the “clear, hold, build and transfer” approach in light of the structural challenges to each element and the pressure to deliver results in a short time-frame amid difficult security conditions.