The Raspadalica Cliff is an almost vertical 100 m high limestone cliff with a railway line at its foot and is known for numerous rockfall occurrences in the past. This article presents the results of the geotechnical study of the cliff based on a traditional geological and geotechnical field survey and remote sensing analysis. Both the traditional geological and geotechnical field survey and remote sensing surveys and analyses enabled the establishment of the structural model of the Raspadalica Cliff and the determination of the discontinuity sets and discontinuity features, such as orientation, spacing, persistence, roughness, discontinuity wall strength, aperture, degree of weathering of discontinuity wall, seepage conditions, and the presence and hardness of discontinuity filling. Kinematic analyses were performed on five cliff zones with slightly different structural features, indicating a relatively low probability of typical failures in the cliff rock mass that precede the rockfall occurrences. Although rockfall phenomena from the cliff face are relatively frequent, the kinematic analyses did not indicate a high probability of their occurrence. The aim of this manuscript is to make scientists and practitioners aware that investigation of rock mass cliffs and possible rockfall failures must not be based on usual methods without critical review of the obtained results and consequences. The combined use of traditional geological and geotechnical methods and more commonly used advanced remote sensing methods leads to better modelling, while the analysis of more associated failure modes can explain the triggering of rockfall.