Can a police officer check your mobile phone randomly and go through your private chats and/or web history?

No, as it is against our Fundamental Right- Right to Privacy mentioned under Article 21 and guaranteed to us by the Indian Constitution. There needs to be a Judicial Warrant for such searches, otherwise it would be an illegal search which is against the Constitution & our Fundamental Rights.

Exception to this- Whether there is a recorded reason for an urgency of police intervention or there is an ongoing investigation against the person.

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