In recent years, Security Sector Reform (SSR) has emerged as a key component of international post-conflict reconstruction efforts. At the same time, however, it is becoming increasingly clear that the holistic approach to SSR that is outlined in policy papers is very difficult to translate into effective interventions in fragile states. This paper identifies two competing approaches for a 'contextualized' SSR-agenda: A monopoly model that focuses on restoring the state's monopoly on the means of violence and a hybrid model that seeks to strengthen local community-based security and justice solutions. The paper argues that as a strategy for intervention, the choice is not simply between a top-down 'imposition' of a universal state model and a bottom-up approach of 'working with what is there'. It is also a choice between direct and indirect forms of rule. This makes the dilemma real for liberal-minded practitioners and observers who for good reasons remain reluctant towards the colonial practice of ruling through middle-men. The paper does not offer a solution to the dilemma. When two imperatives pull in opposite directions, 'answers' are bound to be ad hoc: Specific and contextual, rather than principled and generic. The paper does, however, suggest that part of the way forward may be to move towards a more 'entry-oriented' mode of operation that recognizes that the role of external actors is to help establish a space for security and development solutions, rather than to fill that space.