This paper presents an experience report with a junior-level software engineering course at a large southeastern United States research-intensive university. We provide an overview of the course structure and the course project, iTrust, that has been developed by students over 25 semesters. We summarize reflections from faculty, teaching assistants, and students (through course evaluations). From our lessons learned, we present our course improvements as we prepare for the next ten years of software engineering courses. Our main lessons learned are that 1) course technologies have a lifespan and require periodic updating to balance student learning and working with a legacy system; 2) teaching assistant longevity and support is critical to course success; and 3) the value of working with a large, legacy system is a semester long course, is supported by faculty, teaching assistants, and eventually students.