The concept of context occupies a central place in both the comparative education and international development fields. The empirical research makes an overwhelming case for the importance of context to teaching and learning initiatives in ‘developing’ country settings (Barrett 2007; Crossley, 2010). Despite the evidence that ‘context matters’, the concept of context itself often has been taken for granted as an unproblematic concept within international development and comparative education fields, treated as no more than a set of features of the immediate local setting that are to be identified, described and responded to (Stephens 2007). As Cowen argues, “we are nowhere near having sorted out, intellectually, the problem of context” (Cowen, 2006:567). This paper maintains that as well as context itself having been under-theorized, the practical implications of working contextually have been under-researched. It is in agreement with those who have argued for a more relational and process-oriented perspective, one that frames context as the result of interpretation and as “a process or set of relations … not a thing in itself” (Dilley 1999:5). This paper reports on work in progress involving firstly, problematizing context and secondly, operationalising a critical approach to work contextually, within education development research and practice in the small island states of the Pacific region.