This study addresses the instability of wooden trusses assembled with punched metal plates. The instability of compressed wooden elements is a complex problem due to the specific boundary conditions, the timber orthotropy, and the difficult quantification of the defects. This research presents an analytical framework based on the Eurocode approach for predicting the instability of compressed wooden elements, considering the effect of boundary constraints representative of punched metal plates. The general aspects of this research are twofold: (i) proposing an analytical approximate expression for assessing the theoretical buckling load of compressed beams with elastic boundary constraints; (ii) deriving the buckling design curves as a function of the geometric imperfection of the structural element. The authors refer to the constraints exerted by punched metal plates, experimentally characterized to determine the response along the six degrees of freedom. The experimental results were used to generate a high-fidelity finite element (FE) model of the connection, validate it using digital image correlation, and estimate by extrapolation the stiffness properties of a selection of punched metal plates. Additionally, a secondary FE model was developed to simulate the out-of-plane deflection of structural elements with different types of punched metal plates, predict the failure load from static incremental analysis, and estimate the buckling design curves. In conclusion, the research aims to specialize the design method of compressed members according to the Eurocode, taking explicitly into account the boundary constraints representative of punched metal plates. It is found that while the theoretical instability load of beams with elastic constraints closely approximates that of the clamped condition, the instability load under imperfections resembles the pinned condition more closely. This observation leads to systematically higher imperfection coefficients for elastic constraints than pinned conditions.