This paper presents the development of a web application for automated cutting tool selection in machining, addressing the limitations of manual, experience-based choice that is time-consuming and difficult to standardize. The system is implemented as a three-tier client–server application, featuring a Java backend, a PostgreSQL database, and a React frontend. A proposed hybrid decision-making procedure that contains constraint satisfaction (CSP) is first used to filter feasible tool–holder–adapter sets, followed by multi-criteria decision-making (Analytic Hierarchy Process for criteria weighting, Weighted Sum Model and Technique for Order of Preference by Similarity to Ideal Solution for ranking) to select the most suitable alternative. The database combines Entity-Relationship and Entity-Attribute-Value models to store machines, parts, materials, and user-generated technical solutions, enabling the accumulation and reuse of experience. The approach is validated on a semi-finishing turning case of Inconel 718, where the system automatically ranks available sets and generates an order statement.