Contextualism in political theory is the view that factual claims about context are part of the justification of normative political judgments. There are different kinds of contextualism depending on whether context is relevant for the formulation and justification of political principles (methodological contextualism), whether principles are contextually specific (theoretical or substantive contextualism), or whether context is only relevant for the application of principles. An important challenge to contextualism is the problem of critical distance: given that the point of political theory is to justify normative judgments about specific cases, how can the principles actually offer a critical perspective if facts about the context to be evaluated are also part of the justification for the normative judgments? Tariq Modood and Simon Thompson have recently defended what they call iterative contextualism, which combines elements of all three kinds of contextualism in an attempt to avoid the problem of critical distance. The present paper discusses their proposal and whether they manage to provide a way for contextualist political theory to avoid the problem of attaining sufficient critical distance to the cases, regarding which they seek to provide normative guidance.