After more than five decades of conflict in Colombia, it seems that significant political will for transitional justice programmes—in particular reparations programmes—has emerged with the passing of the 2005 Justice and Peace Law, the 2010 election of Juan Manuel Santos and the Victims Law signed in June of 2011. In 2007, a pilot project of collective reparations programmes was initiated with the support of international development agencies. This article uses data from these pilot projects to make some preliminary conclusions about the challenges involved in implementing collective reparations programmes. It provides recommendations on service delivery, community representation and local accountability. Finally, an argument is made for accompaniment in the delivery of collective reparations in order to help mitigate and reconcile the challenges encountered in implementation.