Water precipitation in road slopes, pavements, and shoulders may cause disturbances such as erosion, increase of the water table level, decrease of the carriageway bearing capacity, and so on. Roads are normally equiped with drainage systems that are sized and implemented in accordance with the rules of art. These equipments are used for the collection and quick evacuation of water precipitation estimated on the basis of the return period that is taken into account. Despite that, rainwater can still infiltrate unprotected cut or fill slopes, and pavements for repeated and intense rainfalls, which may cause a raise in pore-water pressure and a decrease of the factor of safety of road slopes. Using laboratory rainfall simulation techniques, infiltration measurements were made on intact samples to determine with respect to soil properties, how cumulative rainfalls cause decrease in apparent cohesion and lead to slope failure. This paper focuses on describing the relationship between the rainfall characteristics, the changes in soil water profile, and the changes in apparent cohesion for sandy clay samples collected on the national road RN3 located in Haiti. For a set of consecutive rainfall events at around an interval of 24 hours, the results prove that when wetting front depth approaches 2 meters or more, the risk of landslide is proportionally high in a soil with apparent cohesion (Ca) initially high and an effective cohesion (c′) relatively low.