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Focussing on the major cities of Brisbane, Sydney, and Melbourne in southeast Australia, this study seeks to determine the environmental factors that distinguish between heavy rainfall events (HREs) and extreme rainfall events (EREs). Using daily rain gauge observations, HREs and EREs are defined for each domain based, respectively, on the 95th and 99th percentiles of wet‐day rainfall for the period 1979–2018. K‐means clustering is applied to mean sea‐level pressure, data from ERA5 to obtain a set of representative large‐scale circulation patterns associated with these events. Composite synoptic maps, mean vertical profiles, and a series of column‐integrated diagnostics are then examined for each cluster and used to compare the environmental characteristics of HREs and EREs. For all three cities, HREs are associated with an upper‐level trough to the west, with large‐scale ascent, positive column water vapour (CWV) anomalies, and strong moisture transport over the analysis domain. For Brisbane and Sydney, the clusters are characterised by a coastal trough/low with moist onshore flow from the Tasman and Coral Seas. For Melbourne, circulation patterns are more distinct, with clusters characterised by a front, a cut‐off low, and an inland trough. Compared with HREs, EREs show a more amplified upper‐level trough, with stronger vertical motion and larger CWV anomalies over the analysis domain. In Brisbane and Sydney, EREs also feature stronger and deeper onshore flow, promoting enhanced moisture transport. A diagnostic termed upward vapour transport, which combines the key ingredients of high CWV and large‐scale ascent, is shown to discriminate well between HREs and EREs in all three domains. In contrast, surface temperature, which is frequently linked to rainfall extremes via Clausius–Clapeyron scaling, shows significant overlap between the different event categories, particularly for Brisbane and Sydney. [ABSTRACT FROM AUTHOR]