Taking stock of media activist initiatives in the Southwest Asia and North Africa (SWANA) region, this article discusses findings from case study research informing the media education platform “diraya.media.” Through participatory methodology, the case studies and the bilingual (Arabic/English) website aim to analyze and strengthen local media literacy pedagogies by learning with and from media activists in the region. This article reports on six case studies of SWANA-based media activist organizations and pedagogical material for the media literacy classroom. The goal is to reflect and discuss the methodological and theoretical ramifications of Diraya as a pedagogical space for reflection and knowledge exchange between media activists and other learners in the region and beyond. Drawing on the participating activists’ experiences, Diraya is embedded in the turn toward radical media education and civic media literacies, contributing to (1) de-Westernizing media literacy education, (2) creating more learning materials based on local activist knowledge as important resources to increase media literacy, and (3) enabling of long-term collaborations by archiving and making public experiences from SWANA-based media activists.