Painting is a physical practice that engages enactive modes of understanding as well as requiring a heightened visual perception and observational skills. This paper argues that by bringing technology into the painting process, tools can be developed that seek to empower this latent intellect and ability that is normally lost when using a computer in conventional ways. This paper seeks to outline principles necessary to build with software in a dynamic way – leaving space for creative observation, discovery and evolution. Specifically by implementing a Digital Painting Interface and software framework to allow for the manipulation of computer graphics through painting and exploring the differences between these two historically antithetical creative processes. From this, an environment can be developed which allows for the freedom to create using either the artist’s hand or the computer’s generative algorithms in addition to producing a range of artistic works neither painting nor graphics programming alone would be able to create.