The paper deals with numerical investigations of load-bearing capacity and fracture behaviour of Cross Laminated Timber at in-plane shear loading. Focus is on shear failure mechanism III, i.e. failure in the crossing areas between flatwise bonded laminations, and on evaluating test methods for that failure mode. In current design provisions, this failure mode is characterised by the rolling shear strength, fv,R, and the torsional shear strength, fv,tor, and therefore testing including both transverse (rolling) shear and torsional shear is needed. Two such test set-ups are investigated, one aiming at evaluating torsional shear strength and one aiming at evaluating rolling shear strength. Full 3D finite element analyses applying a cohesive zone model approach were used to study the strength and fracture behaviour. Failure criteria for structural design, material strength parameters, and the suitability of the two test configurations to determine strength parameters are discussed in relation to findings from the numerical investigations. One main conclusion from the investigation is that expected test results using the torsional test set-up are less size dependent as compared to test results using the transverse set-up. The numerical analyses suggest a very small influence from tensile loading perpendicular to the crossing area, for both test set-ups.