Not trying to do anything shady, my boss is harassing people, he’s done it before and been reported before (multiple times) but his boss always sweeps it under the rug. We’d like to report him to his boss’s boss and maybe even his boss’s boss’s boss.

First question: will a new gmail/yahoo email get caught up in a spam filter and not get delivered?

Second question: obviously the police could track down who sent an email if a crime was committed (I hope) but how likely is it that our IT department (we’re not a high tech company) can figure out who’s phone logged into the gmail account to send said email?

Third question: if IT can figure it out pretty easily, anyone know another way?

Thanks in advance for helping to rid the world of another fat, lazy, lying, bully of a boss.