As the Irish Free State came into being, Egypt too was declared independent. Whilst in Ireland, League membership was rapidly forthcoming, negotiations for Egypt’s accession were protracted, with Egypt acceding in 1937, the last member state to join the League. Chapter Five investigates why Egypt, which was never formally a colony of the British Empire and from 1922 deemed an independent state, was obstructed by Britain from joining the League for fifteen years. This chapter examines the contested relationship between the Egyptian nationalist Wafd party, that sought Egyptian independence, and Britain, that sought Egyptian acquiescence to a treaty of alliance. Egypt’s contested accession to the League reveals the risks that colonial membership to the League posed to British imperial policy, and how Britian could act as a gatekeeper for the accession of their colonies to the League. Finally, this chapter reveals how the actions of another imperial party, Italy, and its growing encroachment into North-East Africa would ultimately lead to a compromise that would see Egypt’s accession to the League.