Nearly all prison visitation rooms in the U.S. feature photo backdrops, painted by the inmates themselves, to be used in inmate portraits. The portraits are in most cases sent to family and friends in “the free world.” The backdrops, typically painted either on canvas or cinderblock walls, often portray beaches, waterfalls, rainbows, city skylines, and other expansive landscapes. What do these aesthetic choices say about inmates’ portrayals of their experiences in prison? What messages are they sending to those on the outside? How are those messages received?