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Abstract Endodontic instrumentation has undergone remarkable transformation over the past century, beginning with rudimentary hand-crafted steel tools and progressing to advanced nickel–titanium (NiTi) rotary systems, thermally treated alloys, and, most recently, artificial intelligence (AI)-enhanced technologies. These developments have significantly improved shaping efficiency, safety, and overall treatment outcomes. This review aims to comprehensively outline the chronological evolution of endodontic instruments—from early hand files to modern AI-augmented systems—highlighting major breakthroughs in material science, manufacturing, kinematics, and digital integration. A structured electronic search was conducted through PubMed and Google Scholar using the keywords (“evolution” OR “advances”) AND (“instrumentation”) AND (“artificial intelligence” OR “AI”). Four major phases were identified: (1) early hand instruments fabricated from carbon steel and later stainless steel; (2) the introduction and standardization of instruments between 1955 and 1981; (3) the rise of NiTi files and the progressive evolution of their generations—marked by improved flexibility, fatigue resistance, and shaping capabilities; (4) the emergence of digital and AI-driven systems, including CBCT-based planning, automated radiographic interpretation, outcome prediction models, and early robotic endodontic devices. Each innovation addressed specific limitations of earlier systems and progressively enhanced clinical efficiency and safety. Endodontic instrumentation has evolved from simple manual tools to sophisticated, biologically integrated and AI-supported systems. This continuous innovation promises even greater precision, predictability, and personalized treatment in the future.