Methods, systems, and apparatus, including computer-readable storage media, for course assignment by a multi-learning management system. The system can receive data from a variety of individual learning management systems offering different courses. The system can use feedback data of a user base for the system to cluster courses by predicted difficulty, and generate, from the clusters, a sequence of courses for a target user. The sequence of courses can include at least one course from each cluster, with courses from a first cluster with a lower overall difficulty measure preceding courses in a second cluster with a higher overall difficulty measure in the sequence, wherein the starting cluster can be calculated according to the estimated level of the target user.