The built heritage is highly vulnerable to destruction, particularly in cases where irreplaceable cultural values are at risk. Over a building's lifespan, various events—ranging from natural disasters to anthropic factors like wars or neglect—can threaten its structural integrity. Such damage can be severe, often leading to the complete ruin of structures. The need for reconstruction introduces a complex set of challenges, both conceptual and technical. Interventions on ruins are subject to interpretation, and any chosen solution must be based on a responsible analysis, with the primary aim of preserving the inherent values of the structure. This article conducts a comparative analysis of various timber roof reconstruction methods, including traditional solid wood techniques, glulam systems, and metal structures, discussing the advantages and disadvantages of each. Real case studies from the Transylvanian region are used to illustrate these methods. The paper also explores a series of intervention principles and addresses the key question: Can the outcome of a reconstruction still be regarded as a monument? Furthermore, to what extent can an intervention be made without compromising the preservation of original and aged values? The reconstructions are examined holistically, accounting for the impact of the new roof on the overall behavior of the building’s structural system. Beyond replicating the historical form, the analysis employs a multi-criteria approach to determine the most sustainable reconstruction solutions.