Rapid slope instabilities (i.e., rockfalls) involving highway networks in mountainous areas pose a threat to facilities, settlements and life, thus representing a challenge for asset management plans. To identify different morphological expressions of degradation processes that lead to rock mass destabilization, we combined satellite and uncrewed aircraft system (UAS)-based products over two study sites along the State Highway 133 sector near Paonia Reservoir, Colorado (USA). Along with a PS-InSAR analysis covering the 2017–2021 interval, a high-resolution dataset composed of optical, thermal and multi-spectral imagery was systematically acquired during two UAS surveys in September 2021 and June 2022. After a pre-processing step including georeferencing and orthorectification, the final products were processed through object-based multispectral classification and change detection analysis for highlighting moisture or lithological variations and for identifying areas more susceptible to deterioration and detachments at the small and micro-scale. The PS-InSAR analysis, on the other hand, provided multi-temporal information at the catchment scale and assisted in understanding the large-scale morpho-evolution of the displacements. This synergic combination offered a multiscale perspective of the superimposed imprints of denudation and mass-wasting processes occurring on the study site, leading to the detection of evidence and/or early precursors of rock collapses, and effectively supporting asset management maintenance practices.