With increasing utilization of Technological Protection Measures (TPMs) to protect digital copyrighted works, legislative changes to counter their misuse become necessary. With this objective, Sections 65A and 65B of the Indian Copyright (Amendment) Act 2012 were introduced. Section 65A delineates the Anti-Circumvention Law for effective TPMs while Section 65B protects the associated Rights Management Information. Several digital watermarking techniques are widely used for different kinds of protection to digital images, video, audio, databases, websites and e-books. The “effectiveness” of digital watermarks is prone to subjective assessment, not only because of their sheer variety in types, techniques and applications but also due to rapid technological advancements that continuously reshape the standard of “effectiveness”. Given this malleability, a case-case analysis of “effectiveness” may involve expert technical knowledge that is beyond legalese, thereby inviting miscalculation in justice due to subjectivity. In this paper, the scope and remedies for effective legal applicability of the aforementioned provisions in the light of certain grey areas are discussed. These include lack of a specific standard of “effectiveness” and invitation of corresponding technical excesses, skewed quantum of punishment, and the need to bring into ambit certain transformations that can lead to infringement without violating existing laws.