Cyclobutanol ring expansions have emerged as a powerful tool to access functionalised five- and six-membered rings and have thus, in particular over the last decade, attracted considerable interest from the synthetic community. Despite the surge of novel methodologies for the expansion of four-membered rings reported, those enabling the expansion to benzofused cyclohexanones (tetralones) remain notably underdeveloped. Herein, the discovery and development of functional group-tolerant, mild synthetic methodologies for the cyclobutanol ring expansion to tetralones is described. Initially, a regioselective N-bromosuccinimide-mediated cyclobutanol ring expansion to heteroaryl-fused tetralones is reported, which is characterised by its notably short reaction durations. Investigations into optimal reaction conditions, the substrate scope, and the underlying mechanism are detailed here. Our understanding gained through these studies culminated in the application of this methodology to the total synthesis of the 5-lipoxygenase inhibitor carbazomycin B. Then, in collaboration with Alessia Petti and Dr Kevin Lam from the University of Greenwich, a mild electrochemical cyclobutanol ring expansion to 1-tetralones was developed. This enabled the extension of the ring expansion substrate scope, as a variety of electronically and sterically different aryl-substituted cyclobutanols were found to be suitable ring expansion precursors. In addition, studies towards the total synthesis of the perfumery agent myrrhone are described.