Ubicomp technology faces many technical challenges, which makes it difficult to test in real world situations. However, understanding and building for everyday practices is crucial for ubicomp designers, in order to push the technological development in the directions needed. We have developed and tested a ubiquitous computing prototype supporting collaborative scheduling. It is based on Pin&Play, a surface-based networking technology with interactive pushpins. The team of a local film festival was engaged in the development process, which resulted in a partial implementation illustrating how their current work practice could be supported. Drawing on this particular design case, we report findings and discuss challenges for ubicomp technology in general.