Headland Bypassing is mainly a wave-driven coastal process that interconnects sediment compartments and allows the continuity of the longshore sediment transport. Waves, in turn, are subject to atmospheric patterns and climate drivers. Hence, this study focuses on identifying the atmospheric systems and associated wave conditions that have triggered bypassing events in Fingal Head (New South Wales, Australia) over the last 33 years. For this, clustering techniques were used to identify 225 weather types that represent the daily atmospheric variability over the Coral-Tasman Seas. Four recent storm events that triggered headland bypassing were numerically simulated including waves, currents, sediment transport, and morphological evolution in order to identify the relevant weather types for the development of the sand pulse. Results revealed that strong low-pressure systems (e.g., Tropical Cyclones and East Coast Lows) occurring off the Eastern Australian coast around 30°S are the dominant patterns triggering bypassing events in the study area. The headland bypassing mechanism was observed to vary between large sandbar systems and sediment leaking around the headland according to slight changes in the sea states generated by these storm events. Overall, atmospheric patterns showed control over when and how the bypassing pulse occurs, whereas sediment availability is the main factor influencing long-term cycles of bypassing that are subject to the variability of El Niño – Southern Oscillation and Pacific Decadal Oscillation. Altogether, this study emphasized the intricacy between the multiple factors controlling headland bypassing events, which has direct implications on the potential for predicting the occurrence of this local coastal process.