Recent advancements in engineering practices and manufacturing methods have enabled the construction of higher consequence mass timber buildings; however, legitimate concerns relating to the fire safety of these buildings persist. Where traditional fire-resistance-based design assumptions may not be appropriate, and given the demonstrated susceptibility of loadbearing timber elements to failure under comparatively mild heating, understanding temperature-dependent variations in the mechanical properties of timber is essential for the fire safe design of higher consequence buildings. This study investigates the influence of structural utilisation (nominally 50% and 20%) and pre-heating moisture content (nominally 0% and 10%) on the compressive response of timber under transient heating. Small-scale specimens were tested in direct axial compression parallel to the grain and subjected to non-charring temperatures until failure. At 50% utilisation, moisture considerably influenced failure temperatures when compared with dry specimens, whereas at 20% utilisation, the presence of moisture appeared to result in differing failure mechanisms. Distinct failure modes were identified between specimen types, attributed to transient thermal and moisture-induced effects. This study highlights and confirms the significance of hydrothermal effects on mechanical response, and the need for further research into the interaction of these factors on the mechanical behaviour of timber structural elements.