Although research in the area of listening processes and strategies is increasing, it still remains the least understood and least researched of the four skills (Vandergrift, 2007). Based on research in listening comprehension, task design and strategies, this article uses a mixed methods approach to shed light on the development of four intermediate English as a second language (ESL) students’ listening strategy use and awareness over the course of one semester. Specifically, we investigate the complexities of students’ listening strategy use by level of language proficiency (low-intermediate to high-intermediate), the impact of repetition on listening strategies and the development of students’ metacognitive awareness.