The number of incidents worldwide where pile tip damage has occurred during driving has accelerated following the growth of the offshore wind sector, and the expansion into areas with increased risk of embedded boulders or partially weathered soft rocks. The process involving pile-boulder-soil contact can be simulated with advanced 3D large-deformation dynamic coupled Eulerian-Lagrangian (CEL) finite element analysis. However, analyses of this nature are highly time-consuming and computationally expensive. The objective of the paper is to develop a generic framework whereby the potential for denting by a boulder can be assessed a priori. The study encompasses four main components to determine the magnitude of force necessary to create plastic damage of the pile tip and what combination of boulders and soil might generate such reactions during pile installation: (a) a parametric 3D FE structural denting study; (b) a parametric boulder-soil 3D CEL study, where prescribed displacements were applied to the surface of boulders embedded in sand; (c) a range of pile-boulder-soil 3D CEL analyses where a deformable pile and different boulder-soil combinations were simulated; and (d) centrifuge model tests involving tip damage from boulders. Simple relationships and charts have been established from the numerical studies and validated from experimental work.