Extraction of resources in remote locations can require temporary haul roads to transport extremely large, slow-moving, indivisible loads (e.g. plant, oil/gas production modules, reactors, weighing in excess of 1000 tonnes) without interruptions. Poor subgrade soils may experience larger cyclic strains and greater cyclic degradation under these conditions than under conventional roads, yet the short engineering life precludes many foundation strengthening options due to cost. As there is little research into this unique situation, this paper synthesises research from a broad range of applications to discuss implications on expected soil response. Reference is made to critical state theory and Discrete Element Method (DEM) modelling to develop fundamental concepts considering particle-scale interactions. Cyclic failure is proposed to be a kinematically unstable process, triggered by shear banding on the Hvorslev Surface, tensile liquefaction or fabric-governed meta-stable liquefaction; the latter is particularly influenced by stress history and anisotropy. This paper finds pore water pressure accumulation under load and dissipation between loads are key to cyclic degradation and furthermore to be dependent upon load duration, principal stress rotation and repetition frequency. For meta-stable, liquefiable soils in particular, inclination of principal stresses is at least as important in assessing failure risk as magnitude of stresses.