This article examines Portuguese official aid (POA) in Guinea-Bissau, based on the experience of a bilateral educational aid Programme--PASEG (2000-2012). It explores the theory and praxis (understood as instructed action) of PASEG as a complex and transversal intervention in a context of fragility and political uncertainty. It discusses the transition from an aid programme which focused mainly on the individual dimension at the school level to an approach which tried to integrate the organisational dimension and capitalise on the enabling environment. Drawing attention to the idiosyncrasy of the political, historical, cultural and social aspects of Guinea-Bissau, the article highlights the tensions which arise in the attempt to reconcile the technical/academic dimensions of project implementation with the political agendas of POA.