This paper offers a comprehensive philological and paleographical examination of two cursive-script (caoshu) paper manuscripts from the ancient kingdom of Loulan, both attributed to a scribe named Chaoji (超濟), whose hand is also identified with Zhang Ji (張濟) or Zhang Jicheng (張濟逞) in earlier scholarship. Discovered by Sven Hedin in March 1901 and first published by Sten Konow in 1920, these documents have since attracted sustained scholarly attention from Japanese and Chinese researchers, including Akai Kiyomi, Lin Meicun, Meng Fanren, Hou Can, Yang Daixin, and most recently Chen Ling, Zhang Yongqiang. Despite decades of study, significant disagreements persist regarding the transcription of numerous cursive glyphs, primarily due to the highly abbreviated and fluid nature of the script, compounded by physical deterioration of the manuscripts. Drawing upon comparative analysis of cursive forms from contemporaneous sources—including Dunhuang manuscripts, Jin dynasty calligraphic models by Wang Xizhi and Wang Xianzhi, Han bamboo slips, and other Loulan texts—this study re-evaluates contested characters in both documents. Key reinterpretations include identifying “虎” (tiger, possibly a personal name) instead of “帝” in “羌虎”; reading “與” (with/to give) rather than “足” or “具” in “與所履”; preferring “夏” (summer) and “享其宜” (enjoying well-being) over “多” and “早其宜”; and transcribing “見兄甚勞” (seeing elder brother, [he is] very weary) instead of “昌弟云”. Each proposed reading is supported by formal glyphic comparison and contextual coherence. The paper also clarifies phrases such as “湌食如常” (eating as usual) and “差錯” (mistakes), reinforcing the semantic plausibility of the new transcriptions. Beyond resolving specific textual cruxes, this study illuminates the high level of calligraphic artistry in Chaoji’s hand and contributes to our understanding of the development of cursive script during the Han-Jin transition, particularly its role as a precursor to later Chinese character simplification. These refined readings provide a more accurate foundation for historical, linguistic, and cultural research into the Silk Road’s eastern frontier during the third to fourth centuries CE.