The government has been working on amending the country’s decades-old Information Technology Act for some time now, and we finally have a rule, IT (Intermediary Guidelines and Digital Media Ethics Code) Rules, 2021. This short article analyzes how the rules though an attempt to regulate the surge in social media and digital platform usage lacks a bit in its execution plans. If compared with IT rules, 2011 these rules also mandate intermediaries to exercise ‘due caution and discretion’ but will let government regulate digital news platform and will also be applicable to OTT content providers. Several proposals in their present form in these rules suffer from unconstitutionality and will undermine free expression and privacy for internet users in India as it is not possible to implement the rules to such wide and critical areas including WhatsApp, Twitter etc., and OTT platforms with crores of users and number of intermediaries in India itself and that too without violating the encrypted privacy of users, as we lack such technology of automated censorship and an uninterrupted regulating system. Issues like obscene contents and pornography in electronic mode have seen legislations and rules earlier too like provisions on ‘Obscenity’ under IT Act, 2000. The difficulty to decide what amounts to obscenity and to differ that from ‘freedom of expression’ is a dilemma encountered by them too and when ‘social media’ is mentioned specifically this process becomes vaguer. Also, including digital media in it is like poking the bear, in this context the bear is “freedom of speech’’. The IT rules, 2021 seems more like making same rules at a same time for a family of fifteen or more members all living at different parts of the world and mandating that each member must follow them within a stipulated time.