Steep alpine rock slopes undergoing deformation may give rise to concurrent landslide hazards of different type and magnitude. The underlying mechanisms of instability are often challenging to investigate due to their inherent complexity; furthermore, they can occur on poorly accessible terrain, preventing the collection of data by means of traditional field techniques or even inhibiting awareness of hazards. This paper focuses upon one such case, in which a major transportation corridor running along the floor of the Aosta Valley (Western Italian Alps) is affected by significant—and until recently unknown—rockfall hazards promoted by a previously collapsed rockslide still deforming slowly at elevations almost 600 m above the road. In particular, two large discrete blocks (volume > 103 m3) lie precariously at the toe of the slide and could fall downslope at extremely rapid velocity. The design of countermeasures for the stabilization or removal of these blocks would require the assessment of their mechanical interaction with the bedrock and degree of internal fracturing (i.e., possible pervasive damage within the blocks). We perform this task by first exploring potential kinematic styles and damage patterns at failure according to a series of preliminary finite-element models. We then use detailed displacement measurements from remote sensing and in situ monitoring, in conjunction with repeat topographic surveying from a terrestrial laser scanner (TLS) and a drone laser scanner (DLS), to reconstruct the actual kinematics of the blocks. The results substantiate the hypothesis that instability is primarily controlled by transient degradation of friction on a through-going basal rupture surface. Development of a large tensile fracture in one of the two blocks is inferred to be conditioned by increased non-planarity of the slipping joint in comparison with the other block. We highlight that optimized integration of cutting-edge rock slope investigation tools can help address otherwise unresolved key aspects of complex instabilities in steep mountainous areas.