A steel-to-CLT connection under moment and shear loading, that led to non-uniformly distributed compressive forces perpendicular to the grain, was investigated in a combined experimental-numerical study. Mechanical tests were carried out for two different positions of the steel plate on the CLT-surface and with two different fiber orientations in the deck-layer. Different CLT-layups with different CLT-plate and deck-layer thicknesses were investigated. kc90 factors for the current engineering design concept for uniform compression perpendicular to the grain were derived from experiments. Experimental findings were used to validate finite element models. An almost deck-layer fiber orientation independent connection resistance became obvious. Only for steel-to-CLT contact connections at the edge of the CLT, loaded by a moment across the grain of the deck-layer, considerably lower resistance was found. A pronounced influence of the CLT-layup and thickness on the connection's moment capacity and stiffness were seen. Numerical simulations were able to qualitatively reproduce experimental findings. kc90 values for non-uniform compressive loading were substantially higher than for uniform loading. Based on the findings, a lower bound design approach that neglects the deck-layer fiber orientation and the CLT-layup might be appropriate for the design of steel-to-CLT contact connections under moment loading.