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Despite global trends to expand the ambit of copyright, Canada and Israel both show promise in cultivating the principal of fairness when exercising exceptions to copyright. Their journeys were led by their highest courts; each sought to shift the dialogue of exceptions from stringent allowance to robust application. Both countries began from the rigidity of fair dealing and considered expansion into the realm of fair use. This exploration is intriguing given that both countries show an uncanny similarity in terms of the manner by which their nation states came into being, their ensuing diversity of population, the mixture of common and civil law within their copyright regimes, their position in terms of the WIPO Internet Treaties (1996), and their relations vis-à-vis the United States. At the time of this writing, the two countries are set to diverge in law but not necessarily in practice.