Transportation infrastructure in mountainous terrain and through river valleys is exposed to a variety of landslide phenomena. This is particularly the case for highway and railway corridors in Western Canada that connect towns and industries through prairie valleys and the Canadian cordillera. The fluidity of these corridors is important for the economy of the country and the safety of workers, and users of this infrastructure is paramount. Stabilization of all active slopes is financially challenging given the extensive area where landslides are a possibility, and monitoring and minimization of slope failure consequences becomes an attractive risk management strategy. In this regard, remote sensing techniques provide a means for enhancing the monitoring toolbox of the geotechnical engineer. This includes an improved identification of active landslides in large areas, robust complement to in-place instrumentation for enhanced landslide investigation, and an improved definition of landslide extents and deformation mechanisms. This paper builds upon the extensive literature on the application of remote sensing techniques and discusses practical insights gained from a suite of case studies from the authors’ experience in Western Canada. The review of the case studies presents a variety of landslide mechanisms and remote sensing technologies. The aim of the paper is to transfer some of the insights gained through these case studies to the reader.