This article identifies and analyses a structural transition in UK equality and anti-harassment law through which normative language originally constraining acts of interference has been progressively extended to constrain evaluative judgment itself. Drawing on close doctrinal analysis of the Equality Act 2010, s 26, university conduct codes, criminal communications statutes, and the Higher Education (Freedom of Speech) Act 2023, the article documents a three-stage pattern: from act-constraint (Stage 1), through an evaluative gateway created by subjective-effect tests (Stage 2), to judgmentas-sanction-target (Stage 3). Case law analysis-spanning Forstater v CGD Europe, Miller v College of Policing, Lee v Ashers Baking Company, Ngole v University of Sheffield, and cognate decisions-reveals that courts have intermittently recognised and corrected this transition, but that the statutory architecture continues to enable it. Comparative analysis confirms that the transition is strongest where legal frameworks provide evaluative gateways and weakest where strict act-speech distinctions are maintained. The article concludes that stable rights-protective frameworks require explicit statutory differentiation between act-constraint and judgment-constraint, and that the 'purpose or effect' formulation in s 26 constitutes a structural vulnerability that legislative reform has not yet adequately addressed.