Windscribe and Remote Work (question for VPN subreddit maybe)

VPN
1

Just checking here first! Though maybe it’s a question for r/vpn or r/sysadmin

Issue: recently my work computer started no longer showing my Windscribe IP. My router (DD-WRT) is configured generally via Wireguard.

Objective: to get the work computer to continue recognizing it. All other devices I connect to the router recognize it and behave accordingly.

Troubleshooting steps taken:

  1. Switched Wireguard ports (all)

  2. Switched to OpenVPN and tried all protocols (UDP, TCP) and cycled through all ports

  3. Connected via cell phone hotspot (VPN connection enabled in hotspot) and cycled through all protocols including Stealth Mode.

4.) After a conversation with Garry, I also tried adding additional options in DNSmasq (some server IP it told me to enter in the field.

5.) With and without #4 implemented I enabled SmartDNS resolver in DD-WRT. This cut all internet connection for me.

I’m guessing this is some issue upstream with either the work networks firewall or some permissible traffic/connection blocking. I just cannot get the work computer to recognize the router-levl windscribe IP, pre- or post- connection to the internal (cisco) work vpn.

Any advice? Thanks in advance!

2

Define “no longer showing my windscribe IP”

And what IP is it now showing? Your ISP IP? A unique unknown IP?

Where are you getting the IP from? The comp settings or detecting it on a website?

3

i’m getting a unique unknown IP (per whatsmyip dot com and similar sites).

4

My guess is that your work computer is running through your work VPN.

So your work thinks you’re connecting from your windscribe IP and do not know about your home IP. But then they are giving you a new IP from their own VPN. This new IP is what public websites would see.

5

yes…overall i think that’s what’s happening here. For a brief moment at startup i get the windscribe IP but then it swaps out after all the corporate IT services get up and running. Perhaps it used to just be a transparent passthrough on their end but now it actually reroutes. Thanks for replying.

6

Yeah this is exactly how the VPN on my work computer acts. It used to use whatever IP my router gave it until I connected to the VPN. Then they switched to an always on VPN and it gets a work IP right after windows boots.