Fwd: Wireguard Win10 Client not work through an openVPN tunnel on the same machine

Sat Feb 27 11:19:16 UTC 2021

Machine A in Intranet Windows 10 Prof Version : 20H2
Address 172.1.2.3
Firewall is open for  webserver und wireguard (8080 tcp, 44444 udp)
is WireguardServer  Version 0.3.7

wg.conf:
PublicKey = A8C8+bRYaqu2MKs2SpwuRRgmwqItYwFFJjk77UtUUxU=
[Interface]
PrivateKey = ********************************
ListenPort = 44444
Address = 192.168.44.44/32
[Peer]
PublicKey = JkacJ6IYPUgCOv+OdHN6ZMJ+JRZr6V5/kDzthil/CUs=
AllowedIPs = 192.168.44.4/32
PersistentKeepalive = 25
--------------------------------------------------------------------------------
Machine B extern over openVPN connected with the Intranet Windows 10
Prof Version : 20H2  (OpenVPN Client running on B)
Address 172.11.12.13 could reach A over Routing  (Test: Webserver on
A: 172.1.2.3:8080)
is WireguardClient Version 0.3.7

wg.conf:
PublicKey = JkacJ6IYPUgCOv+OdHN6ZMJ+JRZr6V5/kDzthil/CUs=
[Interface]
PrivateKey = **********************
Address = 192.168.44.4/32

[Peer]
PublicKey = A8C8+bRYaqu2MKs2SpwuRRgmwqItYwFFJjk77UtUUxU=
AllowedIPs = 192.168.44.44/32
Endpoint = 172.16.41.20:44444
PersistentKeepalive = 25
--------------------------------------------------------------------------------

Result after Activation
The Client B could not estable a working Wireguard-Connetion to A :

Protokoll Server:
2021-02-27 10:53:02.636: [TUN] [44444] Startup complete
2021-02-27 10:53:03.615: [TUN] [44444] peer(Jkac…/CUs) - Received
handshake initiation
2021-02-27 10:53:03.615: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake response
2021-02-27 10:53:07.821: [TUN] [44444] peer(Jkac…/CUs) - Handshake did
not complete after 5 seconds, retrying (try 2)
2021-02-27 10:53:11.480: [MGR] [Wintun] IsPoolMember: Reading pool
devpkey failed, falling back: Element nicht gefunden. (Code
0x00000490)
2021-02-27 10:53:28.626: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake initiation
2021-02-27 10:53:33.794: [TUN] [44444] peer(Jkac…/CUs) - Handshake did
not complete after 5 seconds, retrying (try 2)
2021-02-27 10:53:33.794: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake initiation
2021-02-27 10:53:39.094: [TUN] [44444] peer(Jkac…/CUs) - Handshake did
not complete after 5 seconds, retrying (try 3)
2021-02-27 10:53:39.094: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake initiation
2021-02-27 10:53:44.286: [TUN] [44444] peer(Jkac…/CUs) - Handshake did
not complete after 5 seconds, retrying (try 4)
2021-02-27 10:53:44.286: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake initiation
2021-02-27 10:53:49.549: [TUN] [44444] peer(Jkac…/CUs) - Handshake did
not complete after 5 seconds, retrying (try 5)
2021-02-27 10:53:49.549: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake initiation

Protokoll Client:
2021-02-27 10:53:02.793: [TUN] [test-44444] Startup complete
2021-02-27 10:53:02.836: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake response
2021-02-27 10:53:23.530: [TUN] [test-44444] peer(A8C8…UUxU) - Retrying
handshake because we stopped hearing back after 15 seconds
2021-02-27 10:53:23.530: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake initiation
2021-02-27 10:53:27.815: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:27.815: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:28.815: [TUN] [test-44444] peer(A8C8…UUxU) -
Handshake did not complete after 5 seconds, retrying (try 2)
2021-02-27 10:53:32.982: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:32.982: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:38.283: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:38.283: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:43.475: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:43.475: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:48.738: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:48.738: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:54.066: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:54.066: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:53:59.148: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:53:59.148: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:54:04.459: [TUN] [test-44444] peer(A8C8…UUxU) - Received
handshake initiation
2021-02-27 10:54:04.459: [TUN] [test-44444] peer(A8C8…UUxU) - Sending
handshake response
2021-02-27 10:54:09.601: [TUN] [test-44444] Device closing

Apparently, the only message that the server has received from the
client is the one that was sent to the public address on port 44444.
After that, the client can no longer send a message - but the other
way round it can.

Modifikation

start a Win10 Sandbox on B.
install the Wireguard Client  there with the same configuration like on B
deactivate  WG-Client on  B
the Sandbox could reach A over routing through the running Open-VPN of B
under these conditions, the wiregiard connection can also be established!!

Protokoll Server:
2021-02-27 11:46:04.958: [TUN] [44444] Startup complete
2021-02-27 11:46:05.762: [TUN] [44444] peer(Jkac…/CUs) - Received
handshake initiation
2021-02-27 11:46:05.762: [TUN] [44444] peer(Jkac…/CUs) - Sending
handshake response
2021-02-27 11:46:05.786: [TUN] [44444] peer(Jkac…/CUs) - Receiving
keepalive packet
2021-02-27 11:46:13.757: [MGR] [Wintun] IsPoolMember: Reading pool
devpkey failed, falling back: Element nicht gefunden. (Code
0x00000490)
2021-02-27 11:46:30.795: [TUN] [44444] peer(Jkac…/CUs) - Sending
keepalive packet
2021-02-27 11:46:30.812: [TUN] [44444] peer(Jkac…/CUs) - Receiving
keepalive packet

Protokoll Client:
2021-02-27 11:46:05.050: [TUN] [wg-test-sandbox] Startup complete
2021-02-27 11:46:05.065: [TUN] [wg-test-sandbox] peer(A8C8…UUxU) -
Received handshake response
2021-02-27 11:46:05.088: [TUN] [wg-test-sandbox] peer(A8C8…UUxU) -
Receiving keepalive packet
2021-02-27 11:46:30.093: [TUN] [wg-test-sandbox] peer(A8C8…UUxU) -
Sending keepalive packet
2021-02-27 11:46:30.097: [TUN] [wg-test-sandbox] peer(A8C8…UUxU) -
Receiving keepalive packet

Heiko Kendziorra