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 teacherswhile implementing LOA in authentic educational settings, especiallyan exam-dominant context that is deemed unconducive to LOAimplementation (Carless, 2017). Even fewer have investigated thecomplexity of LOA implementation in such a context with studentsof limited proficiency. The present case study, therefore, focused onunveiling a language teacher’s struggles and strategies when imple-menting LOA in such an EFL context with limited-proficiency learn-ers, as well as students’ perceptions of and engagement with suchLOA practices. Analysis of data from classroom observations andsemi-structured interviews with the teacher revealed three major LOAimplementation endeavors in response to the challenges she faced:(1) breaking down the teacher–student hierarchy to enhance learnerautonomy, (2) tailor-making LOA tasks to align with students’ cogni-tive and proficiency levels, and (3) engaging students with interestingungraded LOA tasks. Results also showed an overall positive attitudeamong students toward such LOA practices. Theoretical and peda-gogical implications were discussed based on such findings, callingfor more nuanced implementations of LOA in relation to specificcontextual and learner characteristics.