Schools are places where the choices made about computing technologies not only reflect their technical requirements but also reflect the philosophical priorities directing those choices. Schools can deploy a startling range of software (i.e., operating systems, databases, office productivity software, and applications software) for specifc teaching and learning purposes. Applications software deployed in schools must be suitable for use by students who are young and often have limited reading and fine motor skills. Back-end software must be robust enough to handle hundreds and sometimes thousands of users concurrently. One issue that faces schools interested in deploying open source software is the number of choices available; there is a wide variety of open source software that is suitable for use in schools. It is intended that this chapter provide readers with entry points to selecting open source software by identifying criteria that can be used by schools to shortlist potential open source software appropriate for their local environments.