This study examined the act of painting as a critical space from which to negotiate the changing technologies and regimes of representation. From the vantage point of the post-digital age, it asked what trouble painting might make for this new visual world order, and more specifically, how painting might survive and indeed flourish among other technologically advanced mediums. As such, it developed an innovative range of techniques and strategies that extended the possibilities of the medium while providing an oppositional, and at times paradoxical structure to the digital networks of our time.