Assessment literacy has been considered as one of the fundamental aspects of teacher education programs. Therefore, over the past decades, a plethora of studies have been developed to realize the essence of teacher assessment literacy and practice. This qualitative study, through a phenomenological approach, attempted to interpret the essence of teachers’ assessment literacy through experiential lenses of language teachers who practiced assessment as one of their professional requisites, and to identify the most influential contextual factors that mediate teachers’ conceptualization of assessment literacy within the immediate context of classroom. Data were gathered via semi-structured, retrospective interviews with 10 language teachers and their reflective essays on assessment practice. The emergent themes extracted from the data revealed that stakeholders’ needs and expectations, teachers’ experiences and intuitions, and their fear of getting stale can steer teachers’ assessment practice and mediate their assessment literacy. The study recognizes a need for a paradigm shift in the consideration of assessment literacy on the part of other stakeholders including students, parents and school principals, in order to have a thorough assessment practice on the part of language teachers.