Accurate thunderstorm warnings in the hours-to-minutes preceding impact are often limited by the complex evolution of the mesoscale atmospheric environment. To accurately capture these complexities, analysis of observations remained central to operational short-term nowcasting predictions of thunderstorms. Over the past 40 years, multiple high-impact thunderstorm events have impacted the Brisbane Metropolitan Area (BMA) of South East Queensland resulting in significant insured losses. Four of these high-impact events were the focus of the following work. These cases included three events that resulted in the greatest insured losses for the BMA, exceeding AU$4 billion (2017) (18 January 1985, 16 November 2008 and 27 November 2014) and a fourth significant event (24 December 1989). Synthesis of previous work indicates that the four high-impact cases occurred during a south-easterly change with strengthening winds ahead of the change, suggesting commonalities may exist that can be exploited for forecasting. This paper provides a detailed observational analysis of the environment and convective storms from the four BMA events to explore discriminating characteristics that may improve the skill of nowcasting. For the four BMA events, significant deep convection was observed along the change for the hours prior to the change’s arrival at the Brisbane Airport, potentially acting as an early indicator of favourable conditions for high-impact thunderstorms. It was found that the timing of the south-easterly change through Brisbane was also highly correlated for all events, occurring within a 90-min window during the mid-afternoon convective heating maximum. Despite the destructive severe weather, upper air conditions were marginal for supporting organised thunderstorms, highlighting the importance of capturing mesoscale processes, such as the south-easterly change. To further understand possible discriminators of the four high-impact BMA cases, a 10-year climatology of the mesoscale and synoptic environment associated with south-easterly change events was developed for the warm season months of November to January. It is shown that although only a small number of events are associated with high-impact BMA thunderstorms, these events share a set of conditions relating to the prechange wind shift, timing of the south-easterly change and radar signatures.