OpenVPN Support Forum

I'm able to login and get authenticated on the OpenVPN client. If I scroll down the OpenVPN client I do see it receives an IP address on the 192.168.100.X/24 network. I try to ping a server IP on the network and it times out. If I perform a tracert for a server IP and it goes out my local internet connection. I reviewed the OpenVPN logs and see,

netsh interface IP set address 23 metric=1
netsh interface IP set address 23 static 192.168.100.55 255.255.255.0 gateway=192.168.100.1 store=active

However, I open windows command prompt and did a route print. I see a 169.254.x.x IP as the interface for all subnets associated with the OpenVPN tunnel. I then did a ipconfig /all and I do see that 169.254.x.x for the "Unknown adapter Local Area Connection 2:" with description "TAP-Windows Adapter V9 for OpenVPN Connect." I tried to issue the command, ipconfig /renew "Unknown adapter Local Area Connection 2", and see the following message

Windows IP Configuration

The operation failed as no adapter is in the state permissible for
this operation.

This issue is happening only on two Windows 11 laptops for my organization that I am aware of. I have a coworker that has a similar model Windows 11 not experiencing this issue. I've checked and ensured we have the same windows 11 updates as well. Any help is greatly appearciated.

Update:

I can assign a static IP of what is observed on the OpenVPN program to the OpenVPN interface then traffic will traverse the tunnel. However, users don't have admin permissions and that wouldn't be an ideal situation as some users are computer challenged.

Last update:

I'm using pfSense as the OpenVPN server with the latest version of pfsense installed. I also tried the latest version of OpenVPN 3.4.3. Since it wasn't working, I went to client export and tried the latest Windows version installer 2.6.7-Ix001, which appeared to work, but didn't inject all of the routes into the route table (one non-critical subnet was missing). I then downloaded the latest version https://openvpn.net/community-downloads/. Not sure what's the difference or why the 3.4.3 won't assign the Windows 11 tap network adapter an IP address even though the OpenVPN logs show it receives an IP. Just posting this incase it could help someone in the future.