Thanks to the axial resisting contribution, inclined screw connections offer a mechanical advantage over connections with purely transversely loaded fasteners. However, the strong coupling between the axial and the transversal behaviour of the screw makes it challenging to predict the actual connection behaviour. Moreover, the presence of polyurethane interlayers for soundproofing or OSB interlayers of light-frame buildings between main members may increase the bending moment component interacting with the axial force in the screw, thus reducing the connection failure load. This paper experimentally assesses the behaviour of steel-to-timber connections, and a parametric finite element model of Winkler non-linear beam is presented and validated. Finally, a simplified analytical model for capacity prediction is presented. The results of the approach currently provided by the Eurocode 5, of an additive model and the proposed analytical model, are then compared with the results of 500 finite element analysis.