This article discusses an action research study that involved the design and delivery of an online training course for teachers of Arabic to speakers of other languages in the Gaza Strip (Palestine). Grounded in Freirean pedagogy, the course aimed to respond to the employment needs of university graduates by creating opportunities for online language teaching. The action research study explored the dynamics at play within the online educational environment, to evidence elements that challenged and/or facilitated effective collaboration between trainers and trainees. This article retraces and discusses the processes through which the course moved from didacticism to engaged critical pedagogy.