This comprehensive review delves into the intricate landscape of cast post retention in restorative dentistry, encompassing historical perspectives, contemporary techniques, and future directions. Examining factors ranging from tooth-related considerations to prosthesis-related dynamics, the review provides a detailed analysis of clinical techniques, including step-by-step procedures, common challenges, and innovative advancements. Technological breakthroughs, such as digital impressions, computer-aided design and computer-aided manufacturing (CAD/CAM) technology, three-dimensional (3D) printing, and finite element analysis, are explored for their transformative impact on precision and customization. The discussion extends to the promising future of cast post retention, emphasising emerging materials, the integration of artificial intelligence in treatment planning, and patient-specific approaches. Implications for clinical practice underscore the importance of individualised treatment planning and the adoption of advanced technologies. Recommendations for future research advocate for comprehensive long-term clinical studies, investigations into AI-driven treatment planning, and a focus on patient outcomes and satisfaction. This review consolidates existing knowledge and anticipates a future marked by enhanced precision, individualised care, and improved long-term success in cast post-retained restorations.