Despite long-standing claims that the bastion fortification of Zbarazh castle follows the Dutch school of military architecture, this article challenges that assumption through computational AI-assisted analysis. While the layout has traditionally been associated with the Dutch system of fortifications—supported by researchers such as Janusz Bogdanowski and Adam Miłobędzki, who placed Zbarazh within the “Polish manner” derived from Dutch models—no prior study has applied quantitative methods to test this attribution. This study employs a computational workflow that integrates AI-based image segmentation, vectorization of the castle plan, and analysis using Rhino and Grasshopper. Using a scanned plan of Zbarazh castle, automatically converted to editable vector geometry for Rhino, the key geometric features of the bastion outline—specifically, the flanked angles and shoulder angles, critical indicators in bastion classification —were extracted and measured. The analysis reveals that the flanked angles range from 73° to 78°, with an average of around 76.4°, which is significantly higher than the typical Dutch range of 60° to 65°. Similarly, shoulder angles range from 93° to 100°, averaging 96.79°, notably lower than the Dutch standard of 102°30′ to 105°. These findings demonstrate a clear and systematic deviation from Dutch fortification geometry. The results suggest a closer alignment with the Italian school, particularly the New Italian system, which aligns with historical references to Scamozzi’s original design. Ultimately, the study not only repositions Zbarazh within a different architectural lineage but also highlights the value of AI-assisted geometric analysis in correcting historical misattributions in architectural heritage research.