Wind-driven rain is one of the most important moisture sources that may lead to moisture damage risks of building envelopes, particularly when the rainwater unintentionally infiltrates into the envelope assembly through defects of the wall components. This paper proposes a stochastic modelling approach to evaluate the impact of rain infiltration on hygrothermal performance of highly insulated wood-framed walls, including an I-joist deep cavity wall, two exterior insulated walls, and a conventional 2×6 stud wall as the baseline wall. The stochastic hygrothermal models of the walls are created based on the uncertainties of material properties and rain deposition factor under different scenarios with rain infiltration deposited at different locations of the wall assembly. The stochastic simulation results show that the rainwater deposited on a water resistive barrier does not cause any moisture damage risk, but there is a significant risk when the rainwater is directly deposited on the exterior or interior surface of wood sheathing, and the interior deposition has the highest risk.