

I guess it depends on the company and their policies. I’ve been an admin in Google Workspace, and it’s almost hard to avoid seeing some of the reports of the metadata of external incoming and outgoing email.
I remember we even had a rule for external emails with a name that employee name. This was mostly to identify and block scammers impersonating the CEO, but would also inadvertently catch a whole bunch of other weird stuff people were doing as well, but that was mostly someone setting up a shadow IT service that would send email with the name of an employee, which we’d then have to chase and figure out.
I’m less familiar with the MDM software running on laptops, it’s possible that each file copied to a thumb drive is logged, so that is totally a risk, but i imagine it would be harder to detect if that’s a common thing that people do at the org.
Idk, I pay my health insurance premiums and then get my coverage denied and have to fight for what I paid for, is that fraud?