This paper proposes a novel scheme titled ‘selective exchange of the worn cutting edge (SEWCE),’ which uses the cutting edge for an extended time by replacing the worn-out edge. This possibility was investigated for single-edge cutting tools for several operations, such as oblique and orthogonal cutting. The unique design of the turning tool incorporating cylindrical inserts was developed, thereby providing new machining possibilities compared to marketed solutions for round inserts. The prototype tool was prepared for the demonstration by using a cylinder with radius rε = 1.5 mm. A detailed analysis of the contact-zone cutting edge was performed considering a theoretical number of edges for different strategies. With this, the possibility for reusing the cutting element by resharpening the rake surface by up to ‘20x’ was achieved. Additionally, round inserts can be efficiently used in this developed scenario by turning them to compensate for the worn parts of the cutting tools. Therefore, by rotating, the deformed section of the cutting tool can be eliminated, and the number of edges can be created, directly reducing tool costs. Ultimately, conserving the health of a cutting tool brings many advantages, such as extending useful remaining lifetime, improving the surface quality and dimensional accuracy of machine parts, etc.