OpenVPN client appears to connect but OpenVPN Status lists no clients

fogelfish · Dec 10, 2021, 1:39 AM

I tried to follow documentation and guides to set up openVPN on PFsense with the aim of securely accessing a Windows Server on the PFsense LAN, via the openVPN tunnel. It's not working.

In my attempt to sort out what's going wrong, I even got confused whether my client is actually connected because even though my openVPN client tells me I have connected, I don't see any clients listed in the PFsense Status : OpenVPN GUI.

Below is output from ipconfig and route print on my Windows 10 client.

ipconfig

Windows IP Configuration

Unknown adapter OpenVPN Wintun:

   Media State . . . . . . . . . . . : Media disconnected
   Connection-specific DNS Suffix  . :

Ethernet adapter Local Area Connection:

   Connection-specific DNS Suffix  . : domain
   Link-local IPv6 Address . . . . . : fe80::6141:f067:b146:f54f%9
   IPv4 Address. . . . . . . . . . . : 192.168.0.37
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . : 192.168.0.1

Unknown adapter OpenVPN TAP-Windows6:

   Connection-specific DNS Suffix  . : <mydomain>
   Link-local IPv6 Address . . . . . : fe80::115c:c51a:7498:f62a%5
   IPv4 Address. . . . . . . . . . . : 192.168.2.2
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . :

Ethernet adapter Local Area Connection 4:

   Media State . . . . . . . . . . . : Media disconnected
   Connection-specific DNS Suffix  . :

route print

Microsoft Windows [Version 10.0.19043.1348]
(c) Microsoft Corporation. All rights reserved.

C:\Users\BrianFogel>route print
===========================================================================
Interface List
  7...........................Wintun Userspace Tunnel
  9...00 1c 42 c6 7f 65 ......Intel(R) PRO/1000 MT Network Connection
  5...00 ff a0 56 72 7e ......TAP-Windows Adapter V9
  6...00 ac c7 37 5d 92 ......VPN Client Adapter - VPN
  1...........................Software Loopback Interface 1
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0      192.168.0.1     192.168.0.37     25
    66.113.99.234  255.255.255.255      192.168.2.1      192.168.2.2    281
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    331
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    331
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    331
      192.168.0.0    255.255.255.0         On-link      192.168.0.37    281
     192.168.0.37  255.255.255.255         On-link      192.168.0.37    281
    192.168.0.255  255.255.255.255         On-link      192.168.0.37    281
      192.168.1.0    255.255.255.0      192.168.2.1      192.168.2.2    281
      192.168.2.0    255.255.255.0         On-link       192.168.2.2    281
      192.168.2.2  255.255.255.255         On-link       192.168.2.2    281
    192.168.2.255  255.255.255.255         On-link       192.168.2.2    281
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    331
        224.0.0.0        240.0.0.0         On-link      192.168.0.37    281
        224.0.0.0        240.0.0.0         On-link       192.168.2.2    281
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    331
  255.255.255.255  255.255.255.255         On-link      192.168.0.37    281
  255.255.255.255  255.255.255.255         On-link       192.168.2.2    281
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
   207.115.89.187  255.255.255.255         On-link   Default
===========================================================================

IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
  1    331 ::1/128                  On-link
  9    281 fe80::/64                On-link
  5    281 fe80::/64                On-link
  5    281 fe80::115c:c51a:7498:f62a/128
                                    On-link
  9    281 fe80::6141:f067:b146:f54f/128
                                    On-link
  1    331 ff00::/8                 On-link
  9    281 ff00::/8                 On-link
  5    281 ff00::/8                 On-link
===========================================================================
Persistent Routes:
  None

PFsense WAN IP: 66.113.99.234
LAN: 192.168.1.0/24
TUN: 192.168.2.0/24

I'm a beginner with only a smattering of knowledge picked up as needed. I can share more info about my configuration as requested, but first I wanted to ask if anyone has any likely causes for what I've described so far. Thank you!