In 2018, thirty one years after the equality rights guarantee in the Canadian Charter of Rights and Freedoms took effect, women won their first Supreme Court of Canada appeal based on sex discrimination under section 15 of the Charter. Quebec (Attorney General) v. Alliance du personnel professionnel et technique de la santé des services sociaux struck down provisions of Quebec’s Pay Equity Act that denied women remedies for sex discrimination in pay that was identified through pay equity audits. Since 1987, the SCC has recognized that systemic discrimination infuses the systems, institutions and relationships of power through which our society is organized. Yet, only rarely do truly systemic cases of discrimination come before the Court and when they do the Court has struggled to apply an appropriately systemic analysis. Alliance marks a meaningful breakthrough. This paper examines how Alliance and its companion case, Centrale des syndicats du Québec v Quebec (Attorney General), represent a strong step forward in protecting against systemic discrimination. It analyzes jurisprudential advances on substantive equality, the role of section 15(2) of the Charter, and bringing a gender lens to the section 1 analysis. Examining the dissenting reasons, the paper also analyzes how the two cases simultaneously highlight the unresolved fractures at the foundation of equality rights jurisprudence that threaten its stability going forward. Finally it reviews a federal legislative initiative and a provincial litigation strategy – both on pay equity – that followed in the immediate aftermath of Alliance and CSQ to highlight the fragility of section 15’s protection in the face of political resistance to substantive equality. It asks whether, in a period of intensifying political polarization, governments have stopped engaging in the “Charter dialogue” when it comes to equality rights.