This chapter explores how Virtual Reality (VR) is transforming the spatial dimensions of painting, building upon historical artistic developments and philosophical investigations. The history of painting is presented as a dialogue between two-dimensional surfaces and three-dimensional space, from early cave paintings perspective to later movements that fractured and broke through the picture plane. These artistic developments are considered alongside philosophical concepts of space, from its conception as an a priori intuition to its understanding as ‘being-in-the-world’ and the relationship between actual and virtual spaces. VR technology offers new opportunities for painters to explore the virtual, creating spatial realities distinct from traditional painting. Contemporary practices are examined, demonstrating how VR can blur the boundaries between physical and virtual space and generate entirely new forms of spatial experience. The chapter concludes with examples from my own explorations into VR, with reflections on the philosophical and artistic implications.