In the realm of law, neutrality is widely hailed as a fundamental principle of fairness, justice and equity; it is also, however, widely criticized as a myth that too often obscures the inevitable reality of perspective, interest or agenda.The principle of technological neutrality, recently articulated by the Supreme Court of Canada when applying copyright law to online activities, seems similarly fundamental in the copyright realm — and equally mythical. In what is now dubbed the Supreme Court’s “Copyright Pentalogy” — five copyright judgments released concurrently by the Court in June 2012 — the unprecedented importance accorded by the Court to the principle of technological neutrality is clear; what remains unclear is precisely what “technological neutrality” means, why it matters, and whether or how it can (or should) ever be attained. This chapter considers the significance of the principle and its potential to guide the future development of copyright law and policy in Canada. Rather than a limited principle of formal non-discrimination between technologies, I argue that technological neutrality must be conceived in a functional sense, shaping copyright norms to produce a substantively equivalent effect across technologies, with a view to preserving the copyright balance in the digital realm.