I work on a corporate laptop that has an infamous root CA certicate installed, which allows the company to intercept all my browser traffic and perform a MITM attack.

Ideally, I’d like to use the company laptop to read my own mail, access my NAS in my time off.

I fear that even if I configure containers on that laptop to run alpine + wireguard client + firefox, the traffic would still be decrypted. If so, could you explain how the wireguard handshake could be tampered with?

What about Tor in a container? Would that work or is that pointless as well?

Huge kudos if you also take the time to explain your answer.

EDIT: A lot of you suggested I use a personal device for checking mails. I will do that. Thanks for your answers!

As someone who works in corporate IT and dabbles in the security side too: don’t.

People do it and I don’t understand why. Use your personal cell phone or whatever else.

We have logs of everything that goes on that device and we could do more if we so desired. So treat every corporate device as a spy on everything that goes on in it.

We view logs only when incidents happen and they do and it never looks good on the employee who was doing X. I get people who browse Snapchat and YouTube off hours and then click an ad and invite crap into the device and now we see everything you were doing after hours when we do the investigation into the incident. But we do also get alerts about other things, so you never know when someone will pull in something.

And things that seem innocent to you may not to your corporate employer or just those technicians like myself who have access to the logs and could use it against you.

Moral: don’t do anything but work things on company devices.

I’m curious on how your systems would handle something like a guacamole instance running on a users home network? It’s pure http traffic afaict, but I’ve always been curious how it would be logged.

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Depending on the set up, but there should be something that logs all network connections. So they can see the connection to the private IP, just can’t see what it was

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Thank you for sharing this info. It’s very convincing and well argumented.

I won’t try anything else and will use my personal device.

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