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This paper discusses the key legal issues arising from the constitutional conceptions of both the EU and the UK in the latter’s withdrawal process. It argues that the adherent Brexit dilemma is mainly the result of the UK’s non-codified constitution on the one hand, exposing legal uncertainty over institutional procedures, regional involvement, or the precise status of international law. Nevertheless, the EU’s composition of the withdrawal process as defined in Article 50 TEU has also caused confusion during the negotiations of the withdrawal agreement, the future EU-UK relationship, as well as the possibility of revocation. Due to its unprecedented nature, the several uncertainties and flaws inherent in this case have consumed valuable time and resources which could have otherwise been used more efficiently in order to ensure a smooth and orderly departure from the EU.