This anthology investigates the interconnections between painting, photography, and the digital in contemporary art practices. It brings together 15 contributors, including internationally acclaimed artists Matt Saunders, Clare Strand, Elias Wessel, and Dan Hays, to write about a diverse range of art-making involving medium cross-over. Topics discussed here include reflections on the painted-on-photograph, reordering photographs into paintings, digital collage, printing digital landscapes onto recycled electronic media, viewer immersion in painted virtual reality (VR) worlds, photography created from paint, and the “truth” of the mediums. Underpinned by significant theoretical concepts, the volume provides unique insights into explorations of the mediums’ interconnectivity, which questions the position of the traditional genres. As such, this book is essential reading for practitioners, theorists, and students researching the nature of painting, photography, and digital art practices today.