A number of international timbers of high commercial importance are extremely difficult to glue, which is significantly hindering access to global market opportunities for engineered wood products, especially for heavily demanded structural products. Some particularly problematic timbers in Australia are the dominant commercial hardwood species, including spotted gum (Corymbia spp.) and Darwin stringybark (Eucalyptus tetrodonta). These species are renowned for their very high mechanical properties, natural durability and attractive aesthetic appeal. However, they are notoriously difficult to glue, especially for sawn laminate-based engineered wood products, such as structural glue-laminated beams. Despite considerable effort and testing of diverse internationally established best-practice approaches to improve adhesion, glue-laminated beam samples of these timbers still frequently fail to meet the requirements of the relevant standard, mainly due to excessive glue line delamination. This paper discusses the key barriers to effective adhesion of these high-density timbers and particularly emphasises the necessity of achieving greater adhesive penetration. Greater adhesive penetration is required to enhance mechanical interlocking, entanglement and molecular interactions between the adhesive and the wood to achieve stronger and more durable bonds. Potential solutions to enhance adhesive penetration, as well as to improve gluability in general, are discussed in terms of their likelihood to satisfactorily prevent delamination and the potential to be applied at an industrial scale. This new fundamental understanding will assist the development of solutions, allowing industry to commercialise newly engineered wood products made from high-density timbers.