Flow-like landslides triggered by rainfall are a major concern in the peri-Vesuvian region of southern Italy. On December 19th, 2019, a landslide occurred along the Crocelle slope (Sarno Mountains), which had previously experienced a similar event in February 1986. This study was conducted to assess the characteristics of this event in terms of triggering and propagation conditions and, with reference to the 1986 landslide, to evaluate the evolution of residual landslide hazards at recurring landslide sites. Data collection included field surveys, visual analysis of a Unmanned Aerial Vehicle (UAV)-based photogrammetric model, geotechnical laboratory testing, rainfall and slope stability analysis, and propagation modeling. Results suggest that the landslide i) originated below a trail, ii) involved an initial volume of 450 m3, which did not significantly grow due to the limited entrainment of slope sediments, iii) was initiated after 13 h of rainfall (return period ∼4 years), and iv) propagated along a channel with an estimated velocity of up to 10 m/s. Comparison of the 2019 event with the 1986 event revealed a significant difference in terms of landslide magnitude (i.e., volume), potentially due to the occurrence of multiple events, which may have led to the temporal depletion of available materials along a slope repeatedly affected by landslides, and possibly to the different behavior of primary layered deposits (involved in the 1986 event) compared to reworked deposits (involved in the 2019 event). This suggests a reduction in the residual landslide hazard associated with a decrease in the expected magnitude and frequency of prospective events.