This study aimed to gather insights from primary teachers in Fuvahmulah City, Maldives regarding the challenges they encountered while implementing differentiated instruction (DI) in their classrooms. Qualitative research methodology was employed, with data collection primarily conducted through face-to-face interviews using Zoom, a teleconferencing application. Purposive sampling was utilised to select a total of five participants from one primary school who had extensive teaching experience and had experience differentiating their instructions. The collected data was thematically analysed to extract meaningful insights for discussion. The research findings reveal three challenges faced by the teachers, namely (i) resources and support, (ii) classroom and class structures, and (iii) teachers’ pedagogical content knowledge. This study extends the current understanding to include the need for technological support and context-based pedagogical knowledge on DI for teachers to effectively differentiate their instructions.