This study utilized elements of technology-rich ethnography to create a rich description of a multi-user virtual environment in a high school computer programming class. Of particular interest was the transition that took place in classroom culture from one characterized by a well-defined problem solving approach to one more indicative of open learning environment. Using technology, high school students created learning activities and resources for use by younger students in the virtual environment. Evidence supported that high school students initially benefitted from the new open environment; however, some immutable elements of the classroom environment presented barriers to peer collaboration and motivation for high-level, creative work. Our findings lend support to the argument that teachers in high school computer programming classes should incorporate the following features in their curricula: open-ended problem solving, real-world clients, group work, student autonomy and ample opportunities for student creative expression.