After more than 300 years of being exposed to human and nature actions the Master Gate of San Francisco in Almeida, Portugal, has sustained visible extended damage. Although its importance, as a historical monument, is undeniable, no attempts have been done so far to determine its level of safety. In this article, several models are developed in order to achieve this goal. A brief description of the Gate’s history is presented followed by a summary of the inspection and diagnosis procedures employed in this study and the results obtained from them. Later, the type of numerical models selected are discussed as well as the methodologies used to represent damage. Finally results from the numerical models are presented in a first attempt to identify the safety level of this historic construction. Results indicate that although the structure has lost a great percentage of its original capacity is still safe.