This article recounts my experience in enhancing my students' boredom regulation by designing, implementing, and evaluating a strategy instruction project. The project was undertaken with 25 Thai university students enrolled in my English oral communication course for 15 weeks. The project began with exploring how and why my students experienced boredom in my classroom and their habitual boredom coping strategies while examining and modifying the initial design of my strategy instruction. Between weeks 8 and 12, I implemented five boredom regulation strategy sessions by using reappraisals and boredom coping as key components. Students engaged in guided practice, developed their own boredom regulation strategy toolkit, shared their ideas with peers, and reflected on their strategy use. Triangulating data from whole-class surveys, focus group interviews, and the toolkits, I illustrate the positive impact of the project shown on my students' boredom regulation and on my teacher-researcher development, despite the challenges associated with the complex nature of boredom regulation in an authentic instructional setting. This study sheds light on the ways that students and their teacher can work together to cope with boredom in second language (L2) classroom learning.