The Digitally Drawn Art System is the result of on-going doctoral research on Street Art and Design, which has been running for the past three years in the Department of Product and Systems Design and Engineering (D.P.S.D.E.) of the University of the Aegean. In this paper, the latest version of the DDArtS system (version 3) will be used for the first time in a test performed in real-world conditions with the purpose of generating a large-scale outdoor mural. The leading ambition of this doctoral research in general, as well as of this specific experiment, is to investigate whether the use of the design can provide an auxiliary role in the creation of Street Art. In this regard, the project is divided in three main phases, the objective of each phase is to complete the same mural, but in a different way each time: in the first phase, a group of undergraduate students of the D.P.S.D.E. painted the mural using existing traditional techniques to transfer the original design from small to large scale on a wall. In the second phase, one of the authors, an experienced street artist, pained the same mural directly on the wall, without using measurement or transfer techniques. In the third phase, the students and the artist painted the mural, only this time based on an outline sketch generated by the DDArtS system. The completed murals are compared in terms of colour and line quality, but also in relation to the original design. The completion time of each phase will also be documented, as well as the quantity of resources used for each phase and the degree of difficulty during the execution of each mural project. For this purpose, commentary from the participants' experience before, during and after the completion of the three phases of the experiment is included.