Cooperative learning occurs when students work together in small groups on an assigned project to achieve learning objectives. A classroom assignment given in an English for Specific Purposes course namely, Workplace Communication III, exposed medical students to this method. This assignment required students to produce a Web TV program and upload it to YouTube. In completing their assignment by employing cooperative learning method, the students applied several processes and faced challenges that eventually helped them to improve their communication skills in the English language. This study aimed to identify the challenges faced and the strategies the students employed to overcome those challenges. Seventeen first year medical undergraduates who enrolled in the Workplace Communication III course were involved in this study. Semi-structured focus group interviews and reflective notes were used to collect the data for this study. The challenges faced by students are time constraint, communication and technical difficulties, and a lack of creativity and confidence. The main strategies applied included brainstorming ideas, independent learning, and practices to overcome these challenges. This study could serve as a guideline for the course designers to improve the current course.