Some of the most exciting progress to address central limitations in GIS is currently originating from the margins of cartographic traditions. This article explores the potential of a proactive engagement with mapping technologies from peripheral positions, such as humanist, feminist, decolonial, queer, and black perspectives, to overcome what we identify as five intrinsic challenges of GIS: the representation of place; emotions; scales; time and change; and relational approaches. The proposals deal with specific concerns that do not fit in existing GISystems and suggest how a creative engagement with mapping technologies further expands our understanding of what GIS could be.