The decision to leave Afghanistan on foot, and cross Iran and Turkey into Europe - with 250 US dollars (USD), a knapsack, and a dream of better future - warrants close ethnographic scrutiny. Over a million people, nearly a quarter of whom are Afghan, left their homelands seeking asylum on European soil in 2015 alone.1 Among these is Akbar, a young Afghan man who left Kabul in early June 2015 and, three months, 7,000 km and 7,000 USD later, arrived in Frankfurt, Germany. In early May 2016, he anxiously awaits news of his asylum application in a refugee hostel. This article traces his family’s history as refugees beginning with the Soviet-Afghan war nearly four decades ago, and details the costs and the abuses Akbar experienced enroute to Europe. We conclude: first, four decades of conflict shape how Afghans evaluate current circumstances and possible futures; and second, after the devastating toll - emotional, physical and financial - of the journey itself, the forced repatriation of asylum seekers would add yet one more vulnerable group into the country’s instability.