The rapidly growing demand for incorporating the latest technological developments in language pedagogy has contributed to scholars’ devoting more serious attention to web-based assessment (WBA). That being so, this study set out to uncover perceptions of four groups of stakeholders who had been involved in WBA via Moodle since 2018 regarding its challenges and opportunities in the context of English as a Foreign Language (EFL) instruction. To this aim, a convenient sample of nine students, seven parents, eight teachers, and three curriculum designers at an Iranian private language institute was recruited to be interviewed. The results of the study suggested that the perceived challenges were the insufficient provision of technical support, lack of security, low-speed internet connection, the need for teachers’ presence during the exam, lack of provision of intrinsic incentives for learners, lack of detailed feedback, and complexity of online test development. The opportunities, on the other hand, were perceived to be well-suited computer and internet literacy, educators’ competency in the utilization of online educational resources, absence of computer and internet anxiety, provision of immediate feedback, and access to items and responses after the exam.