This study examines the five-century evolution of Cancellaresca Corsiva (Chancery Cursive) script from its emergence in the 16th century to its modern incarnation as Formal Italic. It focuses on the organic link between the script's formal transformation and the fundamental shift in teaching paradigms. The analysis begins with the style's formation in the Renaissance through manuals like La Operina (1522) and printing technology. It then traces its 20th-century transformation into Formal Italic via Edward Johnston's historical reconstruction and Alfred Fairbank's pedagogical systematization. Finally, the evolution of teaching methods—from the master-apprentice model to standardized curricula and digital platforms—is analyzed. The findings reveal that the evolution of Chancery Cursive is not merely an aesthetic change. The script's differing identities as a "craft," a "discipline," and a "network-based practice" have been shaped by its capacity to adapt to dominant modes of knowledge transmission and teaching methodologies. This integrated approach supports the thesis that the survival of a calligraphic tradition depends not only on preserving its aesthetic value but also on its ability to reinterpret the pedagogical tools of each era. Consequently, by blending its layered heritage with historical consciousness and digital possibilities, Chancery Cursive is poised to remain a sustainable reference point for future calligraphy education and typographic design.