This editorial offers critical reflections on short story writing in South Africa post-2000. Against the background of critical scholarship on the short story form and thematic trends of short story anthologies since the late 1980s, we argue that short story criticism on apartheid as well as contemporary South African short story writing has consistently emphasized the genre’s disposition to capture the fragmented realities of socio-political transitions in the country. Critics have frequently observed a shift from the overtly politicized short story of the 1970s and 1980s to a return to a more literary and modernist aesthetics in the present. In this special issue, we intend to complicate this reading by mapping out other trajectories the short story has taken in recent years, which point toward the emergence of more popular subgenres such as speculative fiction, crime fiction, and erotic fiction. Short stories also increasingly examine and challenge conventional sexuality and/or gender-based norms.