Stormwater management is of concern to public institutions and academies. In the Asso Torrent endorheic basin (Salento peninsula, Southern Italy), a network of natural and artificial channels crossing urban and rural areas and flowing towards six swallow karst holes, several floods occurred in the last six years, after the end of extensive hydraulic works. In this paper, the results of an observational study on the meteorological and hydrological factors concurring to these floods are reported. It was inferred that soil saturation, cumulative precipitation anticipating the events, and clogging of the swallow holes are of relevance and must be considered in the definition of new criteria in decision-making procedure. The adoption of both innovative modeling techniques and real-time control should be an efficient solution to properly regulate the flow control devices before and during the precipitation events. With a view to providing solutions for a sustainable management of the water resources, easy-to-implement measures are suggested, such as the selection of flood-tolerant crops and construction of harvesting systems for alternative water uses.