This article addresses recent work on empire and colonisation which calls for a reappraisal of how agency and resistance manifests among groups responding to structural marginalisation. We argue that approaching these questions from within the colonial order reveals important idiosyncrasies regarding how groups understood resistance, agency, and popular organising as possible responses that emerged from within imperial landscapes. Using the example of race as a central regulatory category and practice of colonial power, we analyse two cases which we suggest benefit from an account of agency and resistance within colonial order: the Black Loyalists in English America and the Indigenous royalists of New Granada, two groups which pursued emancipation by choosing to remain under colonial rule. The resulting analysis produces a more dynamic account of resistance and emancipation which responds to the far-reaching influence of colonial order for resistance movements at local, national, and international levels. This account contributes to recent debates which call for theoretical analysis of “middle actors” and popular thinking as it relates to international politics, postcolonial movements, and studies of empire.