Remote sensing technologies and Geographic Information Systems (GIS) have sparked diverse conceptual and critical responses, with feminist approaches in particular undergoing notable transformations. This article traces and contextualizes these changes, emphasizing the re-evaluation of the concept of “distance” in feminist critiques of remote sensing (RS) and GIS from the 1990s onwards. It highlights a shift from outright rejection of GIS/RS technologies as tools of masculinist, positivistic science to a redefinition of remotely sensed information and imbricated understandings of distance and proximity. The article argues that researchers view issues of masculinism from markedly different perspectives and re-evaluate the role of technology-mediated seeing and imagining, resulting in a re-evaluation of physical distance in its relationship to infrastructure, access, and care. What has transformed is what it means to be “critical” toward as well as the possibility to be “critical” with remote sensing from a feminist point of view.