Digitisation and the use of artificial intelligence in tax administration have brought immense benefits to both the assessees and the government: ease of compliance for the former and reduced collection and enforcement costs for the latter. At the same time, they have raised significant concerns about the changing paradigm in adjudicatory jurisprudence. The principles of natural justice and fair play have evolved through the judiciary to protect individuals from arbitrary state action and to ensure equity, reasonableness, and fairness in all spheres of state action. The safeguards that had evolved for ensuring procedural due process were based on traditional adversarial adjudication, which was premised on the physical adjudication process. E-Adjudication is a shift in legal processes from the physical to the virtual realm, changing the nature of the relationship between the parties to the dispute. This presents a compelling case for re-examining the principles of natural justice, considering the evolving nature of the digital adjudicatory system, to achieve a fair, transparent, efficient, and participatory system. The conflict between the new paradigm and traditional principles is best exemplified in direct tax adjudication under schemes such as faceless assessment and faceless appeals schemes. This article examines the points of contestation between faceless adjudication and the principles of natural justice. It maps the legal framework of faceless adjudication and its significant departures from traditional adjudication. It further examines the discord between the principles of natural justice and the faceless adjudication schemes in matters of notice, evidence, legal representation, and hearings. Finally, the article makes observations about the evolving nature of the digitised adjudication framework and the challenges it poses to traditional principles of natural justice.