For this dissertation, I had the opportunity to investigate a well-established university-based intensive English program in the northeastern United States as it transitioned from an integrated-skills to a paired-skills approach. My goal as a researcher was to investigate in what ways "listening," the second language (L2) skill researchers view as the least understood and the least practiced (Field, 2019; Graham, 2017; Graham, Santos, & Francis-Brophy, 2013; Siegel, 2018; Vandergrift & Goh, 2012), was receiving attention, programmatically as well as pedagogically, in the new paired-skills approach, and how that attention manifested in the classroom. Toward this goal, through interviews with program leaders and experienced instructors, I explored what they considered as key pedagogical challenges and opportunities in L2 listening in the earlier integrated skills program and in the new paired skills program. Through classroom observation, I documented how instructors approached L2 listening pedagogy in the new paired-skills program. Analysis of instructor interviews showed that instructors described using a wide variety of content-based approaches when teaching L2 listening in the integrated skills approach. In the new paired-skills approach, they described encountering many challenges with L2 listening pedagogy they had yet to resolve. Analysis of classroom observations in the paired skills program revealed that instructors mostly structured lessons with before-listening activities, with a preference for activating background knowledge via vocabulary preview and discussion based on textbook themes. A synthesis of case study findings across program leaders and instructors revealed that teachers structured different kinds of listening experiences for students but did not engage in explicit instruction in L2 listening focused on specific features of bi- and multi-directional spoken language nor did they offer much during listening instruction. Overall, the findings suggest the need to develop more curricular and professional development materials to assist instructors in further developing L2 listening pedagogy, curriculum and assessment in their classroom instruction. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]