This paper investigates the mechanical and the hysteretic behaviour of steel-to-timber joints with annular-ringed shank nails in Cross-Laminated Timber (CLT). These fasteners are used to anchor typical metal connectors, such as hold-downs and angle brackets, to the CLT panels. The experimental programme presented in the paper was carried out at the Institute of Timber Engineering and Wood Technology, Graz University of Technology (Graz, Austria). Average and characteristic values of the experimental strength capacities are evaluated and compared to the analytical predictions determined according to current structural design codes and literature. Furthermore, to fulfil the requirements of the capacity-based design, the overstrength factor and the strength degradation factor are evaluated and conservative values are recommended.