Advice Needed: Setting Up a Raspberry Pi VPN for Routing Traffic Before Work VPN

VPN
1

Hi everyone,

I’m considering setting up a Raspberry Pi as a VPN server at home to route my internet traffic through it before connecting to my work VPN. My goal is to have my traffic appear as if it’s coming from a different location for privacy reasons before it hits the work VPN.

Here’s what I plan to do:

  • Set up a Raspberry Pi with VPN server software (likely OpenVPN).
  • Configure my devices to connect to the Raspberry Pi VPN first.
  • Then, connect to my work VPN.

I’m looking for advice on:

  1. The potential pitfalls of this setup.
  2. Whether this could affect my connection to the work VPN negatively.
  3. Any experiences you’ve had with a similar setup.
  4. Ensuring that I maintain a good security posture.

I’m aware of the policy implications and will ensure compliance with my work’s IT policies before proceeding.

Thanks in advance for your insights!

2

I’m aware of the policy implications and will ensure compliance with my work’s IT policies before proceeding.

former systems admin here - so you’ve cleared this with work then? otherwise you aren’t in compliance at all

3

Not sure what privacy reasons you have here. If you want to hide the fact that you are on vacation while you should be at work and available to come to the office when asked then this is a bad idea and they will find out eventually.

Otherwise your workplace knows where you live as they most likely have your personal address on file to send you mail if necessary.

4

If you are trying to hid what country you are in so you can work in a geo-restricted role… your company is going to know about it. For starters, home address? Thats more of a giveaway from your IP address

5

Enjoy being unemployed soon and you wont have to bother with this at all then, problem solved!

6

Use Tailscale and setup an exit node at home.

7

Firstly, I’m not going to nannie you - this is /r/selfhosted and not /r/aita, /r/legaladvice etc. after all.

The potential pitfalls of this setup.

Work might ban access from known vpn providers, work might not like it, work might discipline you etc.

Whether this could affect my connection to the work VPN negatively.

Possibly, see above.

Any experiences you’ve had with a similar setup.

None.

Ensuring that I maintain a good security posture.

Routing work connection via VPN is arguably worse but if the work VPN tech is secure then its secure. They can moan it’s coming in via China or wherever your VPN is but if the VPN is incrtuable its inscrutable - and if work doesn’t trust the security of their VPN stack they shouldn’t use it.

Unethical life-pro tip - if you are trying to do what other imply by pretending to be ‘at home’ when you’re not you’d be far better off leaving work device at home, hooking up a pi-kvm and accessing that remotely.

8

My goal is to have my traffic appear as if it’s coming from a different location for privacy reasons before it hits the work VPN.

More like you want to work from a location that you should not be working from.

Do not delude yourself that you won’t be discovered.

There is no rational reason to use a VPN to try and hide your for WFH location.

9

I apologize for tagging onto this because it isn’t entirely related, however, assuming my workplace has a lax policy of personal devices, no public wifi network (trust me i’m arguing with this), and has not currently blocked access to known vpn. Are there any security concerns I should be aware of using my personal computer over a vpn on their network?

My use case will mostly be downloading/streaming from my home setup over a OpenVPN or similar connection. (during my off clock lunch etc)