Flash floods and debris flows are iconic hazards in mountainous regions with steep relief, high rainfall intensities, rapid snowmelt events, and abundant sediments. The cuesta landscapes of southern Germany hardly come to mind when dealing with such hazards. A series of heavy rainstorms dumping up to 140 mm in 2 h caused destructive flash floods and debris flows in May 2016. The most severe damage occurred in the Braunsbach municipality, which was partly buried by 42,000 m3 of boulders, gravel, mud, and anthropogenic debris from the small catchment of Orlacher Bach (~6 km2). We analysed this event by combining rainfall patterns, geological conditions, and geomorphic impacts to estimate an average sediment yield of 14,000 t/km2 that mostly (~95%) came from some 50 riparian landslides and channel-bed incision of ~2 m. This specific sediment yield ranks among the top 20% globally, while the intensity-duration curve of the rainstorm is similarly in the upper percentile range of storms that had triggered landslides. Compared to similar-sized catchments in the greater region hit by the rainstorms, we find that the Orlacher Bach is above the 95th percentile in terms of steepness, storm-rainfall intensity, and topographic curvatures. The flash flood transported a sediment volume equal to as much as 20–40% of the Pleistocene sediment volume stored in the Orlacher Bach fan, and may have had several predecessors in the Holocene. River control structures from 1903 and records of a debris flow in the 1920s in a nearby catchment indicate that the local inhabitants may have been aware of the debris-flow hazards earlier. Such recurring and destructive events elude flood-hazard appraisals in humid landscapes of gentle relief, and broaden mechanistic views of how landslides and debris flows contribute to shaping small and deeply cut tributaries in the southern Germany cuesta landscape.