This essay examines the way that US secretary of defense Donald Rumsfeld sought to apply one of the central lessons of the Vietnam War to the George W. Bush administration's War on Terror after 9/11. Following the disastrous withdrawal from Vietnam, Rumsfeld had argued that one of the major lessons to be taken forward was that, in future conflicts, the US needed to ensure that the war was portrayed to the public in a way that would ensure ongoing success. The way to do this, Rumsfeld subsequently averred, was to convey a message of perpetual, unstoppable, but not too rapid, progress; victory was at hand, but it would take some time to achieve. As part of this process, Rumsfeld developed an elaborate narrative based around a keyhole satellite picture of the Korean peninsula at night – one half, that of South Korea, bathed in the light of progress; the other, North Korea, nearly completely dark. This photo, Rumsfeld suggested, told you all you needed to know about the fact that the US would ultimately succeed in the War on Terror. In taking this approach, however, Rumsfeld unwittingly revealed an inherent contradiction that has continued to blight the administration of Barack Obama: that there is a very fine line between progress toward an inevitable endpoint of victory and progress toward a position whereby the US is able to withdraw. For Rumsfeld, progress was toward an endpoint of victory and it was only the change in political context after 2006 that derailed his attempts to set out this message; for Obama, on the other hand, progress has become a prerequisite for getting out of Afghanistan and Iraq.