A system is something that can be separated from its surrounds, but this definition leaves much scope for refinement. Starting with the notion of measurement, we explore increasingly contextual system behaviour and identify three major forms of contextuality that might be exhibited by a system: (1) between components; (2) between system and experimental method; and (3) between a system and its environment. Quantum theory is shown to provide a highly useful formalism from which all three forms of contextuality can be analysed, offering numerous tests for contextual behaviour, as well as modelling possibilities for systems that do indeed display it. I conclude with the introduction of a contextualised general systems theory based on an extension of this formalism.