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This article continues the project to renew the Charter’s methodology of expressive freedom in two parts. Part One explained that the Court’s approach to s.2(b) decision making is skewed against expressive freedom and must be addressed holistically, under ss.2(b) and s.1. (see J. Cameron, “Resetting the Foundations: Renewing Freedom of Expression under Section 2(b) of the Charter”, in B. Bird and D. Ross, eds., Forgotten Foundations of the Canadian Constitution. (LexisNexis Canada, 2022). Part One provided a critique of the current methodology, addressed the meaning of freedom under s.2(b), proposed a revised standard of breach, and sketched a plan for renewal under s.1. That part of the proposal is developed in “Part Two: From the Contextual Approach to Proportionality Balancing”; after a brief recap of the proposal for the breach analysis, the discussion turns to s.1, explaining how a principled approach to limits on expression can be achieved by elevating the role of proportionality balancing. In combination, the doctrinal modifications to the concepts of breach and justification replace elements of the current methodology that are ill-conceived. Though it entails more than a tweak, the proposal to renew ss.2(b) and 1 does not require a wholesale or radical transformation of precedent. The key challenge may be to persuade courts that these modifications align with principles of Charter interpretation and are necessary to safeguard the conceptual integrity of s.2(b)’s guarantee of expressive freedom. This is a pre-publication of a paper forthcoming in the Supreme Court Law Review (2d), and may be subject to editorial revisions prior to final publication.