The underlying complexity associated with deep-seated rock slope stability problems usually restricts their treatment to phenomenological studies that are largely descriptive and qualitative. Quantitative assessments, when employed, typically focus on assessing the stability state but ignore factors related to the slope’s temporal evolution including rock mass strength degradation, internal shearing, and progressive failure, all of which are key processes contributing to the final collapse of the slope. Reliance on displacement monitoring for early warning and the difficulty in interpreting the data without a clear understanding of the underlying mechanisms has led to a situation where predictions are highly variable and generally unreliable. This paper reviews current knowledge regarding prefailure mechanisms of massive rock slopes and current practices used to assess the hazard posed. Advanced numerical modelling results are presented that focus on the importance of stress- and strain-controlled rock mass strength degradation leading to failure initiation. Efforts to address issues related to parameter and model uncertainty are discussed in the context of a high alpine research facility, the “Randa In Situ Rockslide Laboratory”, where state-of-the-art instrumentation systems and numerical modelling are being used to better understand the mechanisms controlling prefailure deformations over time and their evolution leading to catastrophic failure.