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!
Don't. Just fucking don't. Keep your personal stuff off your work equipment and vice versa. I don't know why people keep wanting to do this, because it only leads to trouble.
Anything you do with a company device brings liability to them, which is part of why you should keep things separate, and part of why they manage devices.
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.
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.
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
You wouldn't do this with a stranger's device, so why insist you do it with your employer's device? Just don't.
If you have a workstation and want to use the same monitors/headsets/peripherals with both the company device and your personal device try one or two KVM switches.
I’ve done this in the past without apparent issue. Could you perhaps expand on where the risks arise here? My impression was that unless there is some independent hardware running code separate from the OS, then it would be OK?
It's good to know that they can't bypass wireguard or Tor. I was a worried about that.
As others have suggests, I will probably use a separate device to check my mail. That seems the safest and fairest option both from the company and my perspective.
The computer probably has local security tools (such as an edr) that spy on you any way.
You need to assume it is completely compromised.
But... assuming this isn't in violation of your company computer usage policy (which it very much might be and can put you in trouble) you can install any VPN (avoid spyware shit) and a different browser (ideally something a bit obscure, like librewolf) and this will bypass the MiTM as the the device that does the MiTM would be either:
A) a network device that hijacks the HTTPS requests (VPN bypass this)
B) the browser used by the company
C) some other kind of software that atteches itself to all browsers via admin installed extensions (obscure browser might not be recognised by such software, be sure to check the installed extensions after letting the browser run for an hour)
And once you are done you can check the certificate chain in the browser to confirm.
Before I wrote this thread, I ran for a couple of minutes a browser from a docker container. I couldn't browse any website because of the missing CompanyName CA certificate.
So, I stopped because it was too freaky.
What I did is use a ssh tunnel and rdp over that. ssh and RDP are both build in to windows. VPNs often don't work because some software needs to be installed.
Aside: can you boot off a USB device to have an alternative OS using the same hardware & be okay (assuming there's no TPM/Pluton thingy preventing you)? I would assume weight might be one of the biggest reasons one wouldn’t want to carry multiple laptops, but perhaps a persistent Linux distro or Qubes could be fine to tote around if your back can’t handle it. If the CA is at the OS level, can this be a way to reuse the same hardware?