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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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.
That makes sense, the MiTM was still going on but you browser was not configures with the company CA
Either double-fist with a second laptop or install QubesOS on your laptop
Don’t. And beyond that if you use their WiFi, connect to a VPN. Best just use LTE.
What you are wanting to do is likely a misuse of corporate resources. If you are still unsure go talk to IT
Personal stuff on personal devices.
Company stuff on company devices.
Never mix. I don’t even check my personal email on my work laptop.
If I need access to my home, it’s through an external connection like LTE.
This, but if you use an OS like Qubes then you can keep them separate while still using the same device
I think that with 802.1X you can’t do that unless you export the keys somehow.
If you want to use the same physical device just put Linux on a bootable USB stick and boot off that
Do not do this if it let’s you. Its a good way to get in trouble
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?
Its likely a violation of company policy
Let’s assume it’s allowed. Obviously it’s untrusted hardware, but for widely issued corporate PCs, what’s the risk that there would be some hardware snooping going on if you controlled the OS?
The “snooping” is called a good security policy. Security should always come first.
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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.
Power toys and mouse without borders would like a word
Use a tails usb
Preferably just dont though
I’d its tails then its not an issue at all. Its using the same keyboard but for all intents and purposes, its a different machine
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.
https://lemm.ee/comment/10000283
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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
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.
Use your company laptop for only work…
If you install non-approved software you will probably get flagged by the security team.
Don’t use the company laptop, you can only confirm what is going on with your own devices
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.
Adding on:
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.
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.
If it boots from USB, boot a different OS. But overall, preferrably use a different device.