Contracting in a digital age isn’t just a change in time or place, it is in many respects potentially a change in orientation. Confronting that change initially involved improvising an assimilation of e-contracting into our unstated assumptions about the way contracts are created and the way they are performed, but some adjustment in the framework has been necessary as e-contracting has flourished. It has now been 25 years since the Third Circuit decided Step-Saver Data Systems, Inc. v. Wyse Technology, subjecting box top terms to those assumptions, and 20 years since the Seventh Circuit decided ProCD, Inc. v. Zeidenberg, distinguishing Step-Saver and embracing shrink wrap terms, leading the way to the easy application of click wrap terms. As we have moved from telex to facsimile, to e-mail, to texting, to direct communication between computers, and so on to as yet unknown methods – new technology almost always creates new challenges for contract law. My paper calls for the recognition of new analysis and adaptable principles for electronic contracting on its own terms, but without abandoning the objectives underlying contract law.