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> two employees colluding to exfiltrate sensitive data or something like that

In that case spying Slack usage is simply not enough: the employer should need to spy every single move every employee makes inside and outside the company, which of course it's not possible (well, except if the company is located in a fascist state).



Not everybody is going to send one time pad private key encrypted messages using a 1000 characater password.

It turns out that having access to slack alone would probably catch 95% of situations.




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