The Krbavčići landslide occurred in January 1979 near the town of Buzet, Croatia, after a long period of heavy rainfall. It is located in Northern Istria in the area built of flysch rock mass where numerous mass movements in the past and recent history have been recorded. A flysch rock mass is highly susceptible to weathering, which leads to material disintegration, changes in geotechnical properties, and shear strength decrease, finally resulting in instability processes in flysch slopes. This paper describes existing information about the Krbavčići landslide occurrence, laboratory testing of siltstone samples from a flysch rock mass, and numerical slope stability analyses of a possible landslide reactivation caused by possible long rainy periods and further weathering of the flysch rock mass. Slope stability analysis using the Rocscience, Slide software, as well as landslide numerical simulations using the LS-Rapid simulation software were performed on the basis of the digital elevation model (DEM) and laboratory test results of siltstones with different weathering grades. A DEM of the Krbavčići landslide was obtained on the basis of the unmanned aerial vehicle (UAV) survey conducted in March 2016. The residual shear strength of siltstones to predict a reactivation of landslides is of highest importance and was determined by ring shear and direct shear tests on siltstone samples with different weathering grades. The results of the numerical simulations show that an increase of the groundwater level in the landslide body in combination with the further weathering of the flysch rock material at the sliding surface would have the main influence on a possible landslide reactivation and the further development of the landslide displacement.