The educational use of digital technologies such as mobile devices, computers, and the Internet are progressively replacing pens, books, and the physical spaces known as libraries. Both online synchronous and asynchronous learning modes are emerging as part of the learning styles used with children physically attending schools. Consequently schools and school districts deploy various sorts of software applications to meet the range of teaching, learning, and management functions they perform. As leaders of schools, principals have heightened responsibilities concerning the philosophical directions of schools, as well as aligning the uses of technologies across all facets of their organizations. Set against the backdrop of Australian experiences, this chapter sets out to canvas some of the less considered factors that ought to be taken into account when schools select software applications. Gaining congruence between school philosophies and the technologies used, often-time means open source software ought to be a preferable solution to closed, proprietary software. This argument is justified from pedagogical and management perspectives. Furthermore, it is argued that making informed decisions before adopting the use of a particular technology requires that school leaders understand the educational and technical demands of that technology, and also have a socially-critical understanding of technologies in education and in society more generally. Finally, it is argued that if school principals are willing to consider open source software solutions, the options for teaching and learning with technologies and the strategies for managing the infrastructure of the school in robust and cost effective ways, opens up.