Large scale paintings, the so-called murals, are created by artists on vertical surfaces of tall buildings or walls through procedures that require talent, patience, experience and a lot of attention. Very few art forms can be presented on such a scale. Spatial and environmental constraints when creating a mural, whether under legal assignment or illegally, must be taken very seriously, as they pose many risks and are also defined by various restrictions that the stakeholders need to know and outweigh, throughout the design process. One of the most important, perhaps, spatial restriction in the production of large scale painting projects on vertical surfaces, is the need for transposition and creation of a small draft sketch from a paper or a monitor onto the wall. Before anything else, what usually comes as a first step to approach the problem is to measure the vertical surface. It is necessary to determine the size and position of the drawing in proportion to the surface. It is also useful to make a first delimitation of the area by marking specific points, as for example the corners of the surface, or placing the central or parallel axes. These particular steps are of high importance among others, and the use of technology can assist in their quicker and easier implementation. In this paper, traditional and modern techniques used by artists to create drafts and transfer them on large scale surfaces are being described, along with their specific advantages and disadvantages. Moreover, the contribution of other scientific fields in the aid of this artistic challenge, such as engineering, robotics or programming is listed, followed by certain examples from around the world. Conclusively, in the final part of this paper, the second Version of DDArtS (Digitally Drawn Street Art System) is presented. The systems’ components and functionality is customised to assist the artist on creating a draft for large scale vertical surfaces. DDArtS is scion of the ongoing research being held for the last two years in the interdisciplinary field of Street Art and Design, in the Department of Products and Systems Design Engineering of the University of the Aegean in Syros.