This article aims to explore the contours of Gibraltar, a uniquely situated region in Europe and a non-self-governing British overseas territory. It explores the basis for Gibraltar’s continued and maintained presence within the EU after Brexit. Gibraltar’s full accession into the Schengen area, which was expected to be implemented by the end of 2022, is a significant departure from the disintegration that was observable elsewhere in Brexit negotiations but also does not align with the United Kingdom’s staunch resistance to Schengen more generally. This move will potentially result in Gibraltar having more features in common with what the EU refers to as outermost regions, which are remote areas within the EU where special provisions exist. To that end, this variation in approach by the United Kingdom has placed Gibraltar in an altogether different category of its own and invites new questions about the region’s specificity and status, as well as about the process of disintegration more generally. We argue that Gibraltar’s desire to join the Schengen area has presented challenges to the ongoing predicament of Brexit and has exacerbated its outlier position within the EU. This has given rise to specific questions that this article aims to address: What is the current situation of Gibraltar regarding the United Kingdom and the EU? And, what can the case of Gibraltar teach us in terms of disintegration? This article also examines, from a political science perspective, how reclassifying territories can be employed as a vector to facilitate the United Kingdom’s efforts to disintegrate from the EU, but underscores the ongoing issues surrounding the reclassification of Gibraltar and its people, with every effort to do so proving challenging.