I have my own story about this: In the early 2010's I had a boss that loved to call us and check in every day. We were a remote team and he had anxiety that we were all larking off. I later learned his technique was to open the dropbox admin tools to see the location of someone before calling them. "So, BarelySapient, where are you working at today?", he'd ask in a jovial tone. But in reality, he was testing employee for truthfulness. Every call. He later fired one of my co-workers when they reported to be working from home, but dropbox reported them somewhere in the Florida keys....
There is no way I would send anything to an external print shop from company equipment; they are almost certainly on top of that as well.
If any infosec experts feel like chiming in I'd love to learn more.
Easily detected.
> sharing it as a document via Dropbox or similar
If you use a TLS-inspecting proxy/VPN, this will be detected. Otherwise, it depends on how much monitoring is going on, but at best they could suspect it.
> Copying to physical storage?
At my work, USB drives are disabled by MDM.
You could use transfer the files over SSH. Even if you have an MitM SSH-inspecting VPN, once the SSH channel is established, you could tunnel a second SSH connection through the established insecure SSH session.
Even then, with enough logging, you could detect that all local files were accessed sequentially which would raise a red flag.
There's nothing you can do to prevent insider espionage that wouldn't raise false positives and block legitimate work, but you could at least detect it.
Now, production cost figures and schedules ...
The USB stick they used to make the transfer contracted ransomware from the public terminal, which put everyone on high alert when it was next introduced into the corporate network.