Despite increasing scholarship on learning-oriented assessment (LOA) and the promotion of LOA in various educational contexts, few studies have examined the challenges faced by language teachers while implementing LOA in authentic educational settings, especially an exam-dominant context that is deemed unconducive to LOA implementation (Carless, 2017). Even fewer have investigated the complexity of LOA implementation in such a context with students of limited proficiency. The present case study, therefore, focused on unveiling a language teacher's struggles and strategies when implementing LOA in such an EFL context with limited-proficiency learners, as well as students' perceptions of and engagement with such LOA practices. Analysis of data from classroom observations and semi-structured interviews with the teacher revealed three major LOA implementation endeavors in response to the challenges she faced: (1) breaking down the teacher–student hierarchy to enhance learner autonomy, (2) tailor-making LOA tasks to align with students' cognitive and proficiency levels, and (3) engaging students with interesting ungraded LOA tasks. Results also showed an overall positive attitude among students toward such LOA practices. Theoretical and pedagogical implications were discussed based on such findings, calling for more nuanced implementations of LOA in relation to specific contextual and learner characteristics.