The Indian securities market is, of late, plagued by fraudulent activities such as insider trading and front running, exacerbated by technological advancements such as instant messaging. To combat the same, SEBI had often placed reliance on disconnected circumstantial evidence in regulatory investigations, with the Supreme Court’s progressive deference. However, recent Supreme Court verdicts have reverted to imposing a heavy burden of proof on the securities regulator. As a reactionary measure to these curbs, the SEBI has proposed the draft SEBI (Prohibition of Unexplained Suspicious Trading Activities in the Securities Market) Regulations, 2023, which aim to alter the evidentiary standards in regulatory investigations by incorporating a presumption of guilt in order to facilitate easier prosecutions. In this paper, the authors analyse the changing evidentiary standards in the securities law context, effected through contemporary Supreme Court rulings, in light of the SEBI’s recent attempts to revert to a more permissive evidentiary regime on the probative value of circumstantial evidence. The authors seek to contextualise and speculate as to the intent of the draft SEBI PUSTA Regulations, arguing that they constitute a reactionary measure that must be viewed in light of  restrictive interpretations by the Supreme Court in recent times. The authors provide historical context to the various novel terminologies introduced by the draft PUSTA Regulations by critically analysing them from a constitutional and practical standpoint. The authors further attempt to reconcile the interpretations of ‘materiality’ and ‘price sensitivity’ in light of the draft PUSTA Regulations and contemporaneous proposals relating to the extant insider trading framework.