Over recent decades, the relationship between the United Kingdom (UK) and its Overseas Territories (OTs) has been a generally strong one, with political and economic safeguards in place, bolstered by increasing levels of support from the European Union (EU). Of course there have been strains and tensions in relations, but significant advantages have accrued to the territories. This article takes as its starting-point several key observations made previously by experts in the field and uses them to analyse the condition of relations between the UK and its territories within the context of recent events. In particular, the claim by Godfrey Baldacchino that non-sovereign territories benefit from the support of a “benevolent mainland patron” is considered. Based on a review of recent statements, newspaper articles and policy documents, this article argues that the UK’s benevolence to its OTs has been placed under serious pressure by three recent and unrelated events: the UK’s decision to leave the EU; its sub-optimal response to the damage caused in several territories by Hurricane Irma; and the resolve of the UK Parliament to impose stricter controls on the OTs’ offshore financial sectors.