Azure P2S VPN Gateway not responding on Windows 11

Mark Allison 141

I have set up a Point to Site VPN gateway in my VNet and all was successful, but when I try and connect to it from Windows 11, the connection fails with this error:

A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond. (Error 0x8007274c)

In the VPN client logs I see this error

[cmdial32]	10:37:19	21	On-Error Event	ErrorCode = -2147014836 ErrorSource = RAS

I can resolve the DNS name with Resolve-DnsName of the VPN connection fine, and it resolves to the correct IP Address. I tried a VPN Type set to Automatic and then SSTP but it fails with both.

KapilAnanth-MSFT 48,486 Reputation points Microsoft Employee

2022-10-03T04:38:28.43+00:00
Hi @Mark Allison ,

Welcome to the Microsoft Q&A Platform. Thank you for reaching out & I hope you are doing well.
I understand that you are trying to configure P2S clients with Azure VPN gateway.

I see @Jackson Martins , has made some progress with the Troubleshooting and we can see VPN gateway is not responding on Port 443.

Please make sure there are no NSGs or UDRs in the Gateway subnet

Can you please check if the VPN gateway is in a Succeeded Provisioning state (you can check this under Properties blade)

Also, please make sure the IP you are using is correct and on par with the VPN gateway

Cheers,
Kapil

2 answers

Jackson Martins 10,566 Reputation points MVP

2022-10-02T09:50:45.693+00:00

Hi @Mark Allison
Do you have any virtual adapter on that machine? Because of some hyper-v VM or virtual box?

try disabling all virtual adapters and retest

Here you can find some workaround about vpn client

https://learn.microsoft.com/pt-br/azure/vpn-gateway/vpn-gateway-troubleshoot-vpn-point-to-site-connection-problems

Get in touch if you need more help with this issue.

--please don't forget to "[Accept the answer]" if the reply is helpful--
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Mark Allison 141 Reputation points

2022-10-02T10:11:56.453+00:00

I removed TailScale and Hyper-V feature on my laptop as I wasn't really using it and rebooted but I get the same issue. My network adapters look like this.

Jackson Martins 10,566 Reputation points MVP

2022-10-02T12:30:59.27+00:00

@Mark Allison
Now, Try to uninstalling the Wan Miniport (SSTP) and install again

Mark Allison 141 Reputation points

2022-10-02T12:42:34.247+00:00

I removed all the WAN miniport adapters from Device Manager and then rebooted. I then downloaded the VPN client from the VPN Gateway configuration page and tried again but it's still not working.

EDIT

I also tried on my desktop and get the same issue. I'm wondering if something in my pfSense home router is blocking something?

Mark Allison 141 Reputation points

2022-10-02T13:41:54.837+00:00

On my pfSense router I added a packet capture from my PC to the VPN gateway and packets are showing up there.

10.0.0.79.54396 > 20.0.25.90.443: Flags [S], cksum 0x7154 (correct), seq 363454273, win 64240, options [mss 1460,nop,wscale 8,nop,nop,sackOK], length 0

I also added a firewall rule to pass that traffic and log it, and I can see it in the firewall log.

Jackson Martins 10,566 Reputation points MVP

2022-10-02T15:07:10.97+00:00

can you telnet 20.0.25.90 on port 443?

Mark Allison 141 Reputation points

2022-10-02T19:21:27.233+00:00

I don't have telnet but I tried this in PowerShell

tnc 20.0.25.90 -port 443

and got nothing back

ComputerName : 20.0.25.90 RemoteAddress : 20.0.25.90 RemotePort : 443 InterfaceAlias : vEthernet (HyperV) SourceAddress : 10.0.0.79 PingSucceeded : False PingReplyDetails (RTT) : 0 ms TcpTestSucceeded : False

Mark Allison 141 Reputation points

2022-10-02T20:37:58.387+00:00

It didn't work. I deleted the gateway and recreated it with a higher Sku (VpnGw2AZ) and now it's working. Not sure if it's SKU related or what, but I didn't change anything else my side.

Jackson Martins 10,566 Reputation points MVP

2022-10-02T20:40:26.533+00:00

Thanks for sharing @Mark Allison
For some reason, your gw was blocking your connection.
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KapilAnanth-MSFT 48,486 Reputation points Microsoft Employee

2022-10-06T09:02:08.6+00:00
Hi @Mark Allison ,

Welcome to the Microsoft Q&A Platform. Thank you for reaching out & I hope you are doing well.
I shall post a summary of this thread for better visibility.

I understand that you are trying to configure P2S clients with Azure VPN gateway.
I see @Jackson Martins , has made some progress with the Troubleshooting and we can see VPN gateway is not responding on Port 443.

I suggested you to,

Please make sure there are no NSGs or UDRs in the Gateway subnet

Can you please check if the VPN gateway is in a Succeeded Provisioning state (you can check this under Properties blade)

Make sure the IP you are using is correct and on par with the VPN gateway

You informed me you have deleted the GW and recreated it and there are no issues now.

Cheers,
Kapil
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Azure P2S VPN Gateway not responding on Windows 11

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