The world is converging as a result of technological evolution and integration. The new digital era is emphatically influencing and transforming human lives. The staggering growth in technology has many implications; at one side it brings blessings for the general mass while on the other it makes individuals’ life a hex due to its misappropriation. To safeguard individuals from the realm of digital transgression and to ensure individuals right to privacy, the government of Bangladesh enacted Digital Security Act in 2018. The act has both affirmative and antithetical connotations by supporting penalisation for digital offences conversely barring investigative journalisms and freedom of speech. The present paper is the reflection of the findings congregated from the systematic assessment of the secondary sources. It focuses on the limitations and challenges of the Digital Security Act 2018 by particularly seeing it from the lens of investigative journalism and freedom of expression. Moreover, it also tries to shed light on whether the act has aberrated from its sole purpose that is to ensure security of individual presence in the digital platform. Also, the article manifests the need for an incontrovertible digital security law for the welfare of the citizens.