Masonry structures can be considered as the simplest type of structures concerning its assemblage but, at the same time, it is one of the most complex construction materials in terms of mechanical properties and correct behaviour assessment. In this context, the work herein presented aims at describing an experimental testing campaign recently carried out in order to characterize the out-of-plane behaviour of traditional masonry constructions. Taking advantage of the existence of a traditional two-storey masonry building abandoned after the 1998 Azores earthquake, several in-situ tests were defined and performed with the application of quasi-static cyclic loads at the building top level in the out-of-plane direction. In addition, the efficiency of retrofitting and/or strengthening techniques applied during the 1998 Azores reconstruction process was also experimentally evaluated. Finally, an overall discussion of these techniques is presented, resorting also to previous tests' results carried out by the same authors, aiming at inferring and suggesting quantifications of strengthening techniques' contributions for future interventions on existing buildings. For this purpose, simple analytical mechanical approaches were adopted in order to provide numerical estimates of strength that were found in good agreement with the experimental results.