In this article, I revisit the role of judicial method in contract law. I show how the legal method employed in our common law of contract as a whole (as opposed to that employed in relation to the doctrine of legality specifically) continues to be informed by pre-constitutional legal culture and classical liberal ideology. Accordingly, I argue here that just as the legal culture and underlying ideology must be fully constitutionalised, so too must the legal method finding application in all spheres of contract law (as exemplified by the ‘contract law machine’) be re-aligned with the substantively progressive and transformative goals of the Constitution. At the very least, legal method operating in the constitutional context must reflect the weight that ought to be attached to the foundational constitutional values of freedom, dignity and equality as well as relevant constitutional right(s) and normative considerations that may be applicable in a particular case. Importantly, when constitutionalising legal method, courts need to appreciate the distinction between what I term the internal (content) and external (reach) dimensions of contractual autonomy. In particular, they must be clear as to the legal function of each dimension and how the methodologies pertaining to each influence the legal outcomes of cases.