Teaching Distributed Software Development (DSD) is a challenging task. A convincing simulation of distributed environment in a local environment is practically impossible. Teaching DSD in distributed environment is more realistic since the students directly experience all its specifics. However, teaching in distributed environment, in which several geographically separated teams participate, is very demanding. Different types of obstacles occur, from administrative and organizational to technical ones. This paper describes some of the challenges, lessons learned, but also success stories of the DSD course performed now eight year in a row.