Tarjoma-yi Maḥāsin-i Eṣfahān, translated by Ḥosayn b. Moḥammad Āvī in 729 AH, is a free rendering of the Arabic work by Mofażżal b. Saʿd al-Mafarrūkhī composed in the 5th century AH/11th century CE. Despite its historical, cultural, and literary significance, the Persian version has received little scholarly attention. One of the main reasons for this neglect lies in its syntactic complexity and unusual structures, which make the text difficult to comprehend. This study, adopting a syntactic pathological approach, demonstrates that the difficulties of the text do not primarily stem from vocabulary or rhetorical ornamentation, but rather from obscure and intricate syntactic constructions. The accumulation of such features disrupts the transmission of meaning and entangles the reader in layers of expression instead of clearly conveying the historical content. The methodology is based on syntactic stylistics, analyzing the text sentence by sentence and classifying problematic structures into three categories: verbosity, omission, and dislocation. Examining these features not only facilitates a clearer understanding of this text and similar works, but also contributes to a more precise knowledge of the development of Persian prose in the 7th, 8th, and 9th centuries AH, and lays the groundwork for compiling a lexicon of syntactic structures in classical Persian texts.