Mountainous areas surrounding the Campanian Plain and the Somma-Vesuvius volcano (southern Italy) are among the most risky areas of Italy due to the repeated occurrence of rainfall-induced debris flows along ash-fall pyroclastic soil-mantled slopes. In this geomorphological framework, rainfall patterns, hydrological processes taking place within multi-layered ash-fall pyroclastic deposits and soil antecedent moisture status are the principal factors to be taken into account to assess triggering rainfall conditions and the related hazard. This paper presents the outcomes of an experimental study based on integrated analyses consisting of the reconstruction of physical models of landslides, in situ hydrological monitoring, and hydrological and slope stability modeling, carried out on four representative source areas of debris flows that occurred in May 1998 in the Sarno Mountain Range. The hydrological monitoring was carried out during 2011 using nests of tensiometers and Watermark pressure head sensors and also through a rainfall and air temperature recording station. Time series of measured pressure head were used to calibrate a hydrological numerical model of the pyroclastic soil mantle for 2011, which was re-run for a 12-year period beginning in 2000, given the availability of rainfall and air temperature monitoring data. Such an approach allowed us to reconstruct the regime of pressure head at a daily time scale for a long period, which is representative of about 11 hydrologic years with different meteorological conditions. Based on this simulated time series, average winter and summer hydrological conditions were chosen to carry out hydrological and stability modeling of sample slopes and to identify Intensity-Duration rainfall thresholds by a deterministic approach. Among principal results, the opposing winter and summer antecedent pressure head (soil moisture) conditions were found to exert a significant control on intensity and duration of rainfall triggering events. Going from winter to summer conditions requires a strong increase of intensity and/or duration to induce landslides. The results identify an approach to account for different hazard conditions related to seasonality of hydrological processes inside the ash-fall pyroclastic soil mantle. Moreover, they highlight another important factor of uncertainty that potentially affects rainfall thresholds triggering shallow landslides reconstructed by empirical approaches.