College students who are choosing courses for the upcoming semester must do so in light of their overall degree plan. If they do not, they risk making selections that will ultimately jeopardize a timely graduation. Choosing the right courses, however, requires the student (and their advisor) to know about and properly interpret a myriad of different constraints. At UMW, these include Gen Ed and major requirements, writing and speaking intensive offerings, probable course availability, and a possibly intricate chain of prerequisites that spans multiple semesters of related courses. Failing to properly take into account one of these intertwined constraints can lead to a student failing to enroll in a course next semester that later will turn out to have been necessary for them. And even when these constraints are satisfied, keeping track of them all is tedious and error-prone. The Computer Science Department introduced an experimental web-based degree planning application this spring designed to automate this process. The system helps students build a hypothetical schedule of courses for all future semesters. In addition to a visually appealing drag-and-drop interface through which students can access the entire university catalog, the system automatically checks all of the above requirements every time the schedule is changed, alerting the user to possible problems. The system was piloted to twenty advisors and 81 students during the spring advising period. In this presentation we demonstrate this tool, present findings from the pilot test period, and outline plans for the system’s incorporation into the university advising process.