Şemsi Ahmed Pasha Complex was built in the 16th century by Şemsi Ahmed Pasha, who had served at various state levels for many years. This structure is one of the important structures that should be considered carefully in Ottoman Classical Period Architecture in terms of the qualities it carries. What makes the complex unique compared to other Sinan structures is that the functions are constructed in a different layout plan and also this complex of buildings is the smallest of all such Ottoman constructions. The fact that it is small or that the complex is asymmetric does not depreciate its value, but rather the parts that make up the whole by being shaped together in a balanced and harmonious way make it aesthetic and cause it to have an important place in the silhouette of Uskudar. In this article, the context of the structure and its change over time, the architectural features of the building and the repairs it has undertaken are emphasized. Finally, after the last restoration work, the current damage assessment analysis was carried out. Damage caused by use, moisture-induced deterioration and structural deterioration were determined. In addition, this study attempts to examine the reasons for the damage to the building by use of thermal camera assisted photographs.