this post was submitted on 07 Mar 2024
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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!

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[–] [email protected] 77 points 8 months ago* (last edited 8 months ago) (1 children)

The best thing is to use a different device, period.

Since the company is lord and master over the device, in theory, they can see anything you’re doing.
Maybe not decrypting wireguard traffic in practice, but still see that you’re doing non-official things on the device that are probably not allowed. They might think you’re a whistleblower or a corporate spy or something.

I have no idea where you work, but if they install a CA they’re probably have some kind of monitoring to see what programs are installed/running.

If the company CA is all you’re worried about, running a browser that uses its own CA list should be enough.

[–] [email protected] 9 points 8 months ago (1 children)

Yeah, I'll use my own device, log on to the guest network and start Wireguard on my laptop. Seems a fair choice both for the company and myself.

[–] [email protected] 8 points 8 months ago* (last edited 8 months ago)

That seems more sensible.

But they still can track some of the things you do (same with any untrusted wifi network):

  • all data of http traffic (i.e. non-https)
  • ip addresses you connect to
  • hostnames you connect to (if SNI is not working correctly)