This chapter presents the first analysis of past be regularization in St Helenian English (StHE), the oldest variety of Southern Hemisphere English, with a complex history of dialect and language contact and possible admixture of creolized and restructured second-language varieties. StHE offers new insights into a variable widely documented in English varieties around the world, in a high-contact situation with constraints in a variety that underwent creolization. Based on 16 speakers born between 1916 and 1935, a quantitative sociolinguistic analysis assesses variation and change of levelled was in early twentieth-century StHE. The analysis provides insight into internal constraints, levelling frequency, and external criteria, such as regional origins and gender, and reveals robust individual variation, retracing the origins and evolution of past be levelling in StHE and situating it within a World English context.