This presentation will reflect on my experience of using the OSGeo Live system (versions 5.0 and 6.0) for delivering practical class teaching of GIS at Masters level. We have tried various configurations of the system including virtual machines and running from USB sticks and I will discuss the trials and tribulations of setting up the system to run smoothly on the university's network, allowing the students to transport their work between home and the university and explore setting up data in a spatial database, connecting Geoserver to create web services and then connecting QGIS or OpenLayers to the services to access the services. Alongside discussion of the technical details I will reflect on the wide set of technical skills and system understanding needed to truly understand spatial data management, web service creation and management, and creating a good web mapping site. This poses big challenges for teaching the technology in real depth in the limited time in an MSc curriculum.