Listening is one of the most challenging skills for ESL learners, often underemphasized in instruction and lacking strong pedagogical support. While digital tools offer new opportunities for authentic listening practice, their effectiveness is inconsistent without structured guidance. This mixed-methods quasi-experimental study investigated the impact of technology-assisted, strategy-based listening instruction on 96 adult ESL learners, divided into a control group (traditional textbook instruction) and an experimental group using Ed Puzzle, TED-Ed, and ELSA Speak within a structured three-phase model: pre-task, during-task, and post-task reflection. Quantitative results showed significantly greater gains in the experimental group, especially in inferential comprehension, with large effect sizes. Qualitative findings from journals and focus groups indicated enhanced learner autonomy, increased metacognitive strategy use, and reduced listening anxiety. These outcomes suggest that when digital tools are embedded within a coherent instructional framework, they can substantially improve both listening performance and learner experience. The study contributes to the field of technology-enhanced language learning (TELL) by emphasizing the importance of pedagogical integration, strategy instruction, and reflective learning in designing effective ESL listening instruction