The highways circumnavigating Viti Levu play a pivotal role in Fiji's socioeconomic development, and are a crucial link to transport aid during disasters. Slope failures triggered by heavy rainfall and tropical cyclones have led to considerable damage and fatalities along Viti Levu's main roads in the past. Knowledge of slope instability mechanisms is key for the successful identification and management of slope failure hazards, however, there is a paucity of such information for Fiji's main roads. Severe Tropical Cyclone (STC) Winston was the strongest cyclone on record to make landfall in Fiji and affected the Fiji Islands from the early hours of 20 February until 3 am, 21 February, 2016. We present a field reconnaissance examining the characteristics and mechanisms of slope failures induced by STC Winston along a 35 km stretch of the northern part of the Viti Levu's ring road, “Kings Road”. Approximately 61 distinct shallow, small‐scale slope failures were identified most of which were of a complex type and included earth and debris slides (planar and rotational) with a minor flow component. The trigger for the slope failures was the ~258 mm of rainfall in 24 hours after 30‐days of antecedent rainfall totalling 482 mm. This caused rapid increases in porewater pressures, especially at the contact of residual soils and the underlying weathered basement rock. Evidence of recurring slips along Kings Road indicates that contemporary slope instability is likely caused by elevated porewater pressure during high intensity rainfall events in clay‐dominated soils.