Historic mass masonry forts in the southeast region of the United States of America and the Caribbean experience significant wind forces during hurricanes. These structures, consisting of stone or brick masonry, were generally designed using empirical methods common at the time of construction rather than engineering mechanics for minimum design loads. As the intensity of hurricanes increases, evaluation of these structures is critical to understand their vulnerability. The authors completed a study that evaluated elements of forts for current day and future hurricanes, using present-day design wind pressures. A combined gravity and lateral load analysis was completed to calculate the net stresses in the section of an element. Mass masonry construction relies on net compressive stresses of load-bearing elements. Tensile stresses should be minimal because unreinforced masonry has low tensile capacity. A visual condition assessment of the masonry was completed to inform the analysis. In much of the United States, assumptions, based on prior experience and testing, are generally made for the strength of the masonry. Additionally, the calculated performance for each element analyzed was compared to recorded historic surveys of the structure after major hurricanes. This comparison included reviewing documented damage to the structure as related to the wind pressures during the recorded storm event. Generally, this study determined that the large mass and stiffness of mass masonry structural elements create an inherent resistance to high wind pressures. Isolated components were found to be vulnerable due to their exposure to higher wind pressures and limited structural redundancy. Historic research showed that the elements performed adequately during previous hurricane events, but with wind speeds less than the current code prescribed. Appropriateness of intervention must be considered based on the level of invasiveness to historic fabric and degree of accepted risk for potential damage during a future design wind event.