Cutting parameter optimization dramatically affects the production time, cost, profit rate, and the quality of the final products, in milling operations. Aiming to select the optimum machining parameters in multitool milling operations such as corner milling, face milling, pocket milling, and slot milling, this paper presents a novel version of TLBO, TLBO with dynamic assignment learning strategy (DATLBO), in which all the learners are divided into three categories based on their results in “Learner Phase”: good learners, moderate learners, and poor ones. Good learners are self-motivated and try to learn by themselves; each moderate learner uses a probabilistic approach to select one of good learners to learn; each poor learner also uses a probabilistic approach to select several moderate learners to learn. The CEC2005 contest benchmark problems are first used to illustrate the effectiveness of the proposed algorithm. Finally, the DATLBO algorithm is applied to a multitool milling process based on maximum profit rate criterion with five practical technological constraints. The unit time, unit cost, and profit rate from the Handbook (HB), Feasible Direction (FD) method, Genetic Algorithm (GA) method, five other TLBO variants, and DATLBO are compared, illustrating that the proposed approach is more effective than HB, FD, GA, and five other TLBO variants.