In this paper, a decision support system (DSS) is provided to assist the decision-maker in obtaining the best solution for the transportation problem under uncertainty. Fuzzy parameters of the transportation problem are presented by pentagonal fuzzy numbers. The centroid ranking function transforms these pentagonal fuzzy numbers into crisp ones. Then, a novel, improved greedy method named Dhouib-Matrix-TP1 (DM-TP1) is used in order to help the decision-maker promptly find a suitable solution. Specifically, this DSS is composed of three components: the data base component considers a pentagonal fuzzy number; the Model Base component thinks through the original heuristic DM-TP1; and the User Interface component deliberates the convivial graphical output of the generated transportation plan solution using the Python programming language. Experiments in the literature on fuzzy transportation problems show that the novel proposed heuristic, DM-TP1, is easy to understand and allows the decision-maker to handle transportation problems under pentagonal fuzzy numbers. Also, the DM-TP1 is robust and can be applied to find a feasible initial solution in less time.