Interest in study skills, one of the older realms of educational research, is enjoying a resurgence. Several forces in the field have fueled renewed interest in how learners can best use academic, organizational, and time-management skills to master content. As teacher leaders at a high school, the authors remain in contact with many of their graduates. Graduates are a great source of reflective feedback about their perceived level of preparation for college. While most are satisfied with their content knowledge, many graduates are distressed by their struggle to study independently. Much of this anxiety comes from experiences in online college courses and by the large class sizes of many face-to-face, first-year general education courses. The distress reported by the authors' graduates is mirrored in formal research on perceptions of first-year college students on their high school preparation. Separate study skills courses, decontextualized from the content students are supposed to learn, don't work. The authors recognized that if they were going to foster effective use of study skills, it would need to happen within the context of the students' English classes. The authors would need to infuse study skills and associated self-regulation strategies into content.