Post-earthquake structural damage shows that out-of-plane (OOP) wall collapse is one of the most common failure mechanisms in unreinforced masonry (URM) buildings. This issue is particularly critical in Groningen, a province located in the northern part of the Netherlands, where low-intensity induced earthquakes have become an uprising problem in recent years. The majority of buildings in this area are constructed using URM and were not designed to withstand earthquakes, as the area had never been affected by tectonic seismic activity before. OOP failure in URM structures often stems from poor connections between structural elements, resulting in insufficient restraint to the URM walls. Therefore, investigating the mechanical behaviour of these connections is of prime importance for mitigating damages and collapses in URM structures.This paper presents the results of an experimental campaign conducted on timber joist-masonry cavity wall connections. The specimens consisted of timber joists pocketed into masonry wallets. The campaign aimed at providing a better understanding and characterisation of the cyclic axial behaviour of these connections. Both as-built and strengthened conditions were considered, with different variations, including two tie distributions, two pre-compression levels, two different as-built connections, and one strengthening solution. The experimental findings underscored that incorporating retrofitting bars not only restores the system’s initial capacity but also guarantees deformation compatibility between the wall and the joist. This effectively enhances the overall deformation capacity and ductility of the timber joist-cavity wall system.