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The scale of the injustice inflicted upon the Chagossians by the United Kingdom is self-evident, but their legal route to redress has proven opaque and fraught with difficulty, as illustrated by the House of Lords’ majority decision in R (Bancoult) v Secretary of State for Foreign and Commonwealth Affairs (No 2) [2008] UKHL 61; [2009] 1 AC 453. This disconnect is, nonetheless, inherent in the UK’s constitutional order. Constitutions outline the operation of governance orders, with constitutionalism injecting substantive principles into this picture, developing the relationship between the holders of power and those subject to its exercise. But not all constitutionalising projects are devoted to the same ends. The legal saga of the Chagossians throws into sharp relief the disparity between the imperial constitutionalism which was constructed to organise the governance of the United Kingdom’s colonial possessions in the mid-nineteenth century and the principles which supposedly underpin its liberal democracy in the twenty-first. The denial of substantive protections for a colonised community against unchecked and oppressive exercises of executive power sits uneasily with the prevailing understandings of the United Kingdom’s constitutional arrangements, even though the constitutional architecture of the British Empire was designed to achieve this very end. Drawing upon archival material which highlights how differently the Chagossians were treated from ‘settler’ communities such as the Falklanders, our paper reassesses the Chagossians’ legal struggle in light of the hurdles that this bifurcated constitutional order places in their path, and the significant impacts of their efforts to navigate these barriers to justice upon this constitutional structure.