Modeling is one of the key activities in software and systems engineering as models can serve as placeholders for an existing or planned system, and permit to simplify their treatment by abstracting to problem-relevant aspects. Since 2007, we teach the course “Modeling II” at the Hasso Plattner Insitute at the University of Potsdam on modeling complex IT-systems with UML considering modeling paradigms such as object-oriented, component-based modeling and service-oriented architectures. We report in this paper on experiences from 13 years project-based education in the “Modeling II” course, describe in particular a transitioning from a classic to a more agile project setting, and compare both approaches.