[13] He has represented the India Chapter of Friday's for Future when their website was blocked under terrorism charges.

[18] Gupta is the co-founder of the Internet Freedom Foundation (IFF) and was appointed its first executive director from 2018[19] till November, 2023.

[23] Gupta also filed a case as a petitioner against the Ministry of Home Affairs for disclosure of statistical data on surveillance in India.

[26] On May 31, 2023, he presented Item #7 at the Annual meeting of shareholders of META Platforms[27] titled as, "Shareholder Proposal Regarding Report on Allegations of Political Entanglement and Content Management Biases in India"[28] that was defeated with 5% votes in its favour.

[30] He writes regularly on digital and democratic rights in leading newspapers and is quoted as an expert in India.