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Cannot connect to an external server using a ShrewSoft VPN from an Azure windows machine

Kartikey Sharma 0 Reputation points
2023-02-16T12:26:03.15+00:00

I am trying to connect to an external server (IP address x.y.z.0.1) using a ShrewSoft VPN client. But I always get "negotiation timeout occurred". When I try to do the same thing from my personal machine (outside of Azure VM), I am able to set up the connection and can easily connect to the server. Now I tried to disable all the firewalls in the Azure VM and also set all the inbound and outbound rules in the NSG. Still, I get the same error - "negotiation timeout occurred"

Is this a problem with the Azure firewall settings?

What can I do next?

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2 answers

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  1. Limitless Technology 43,996 Reputation points
    2023-02-17T11:55:04.6266667+00:00

    Hi. Thank you for your question and reaching out. I’d be more than happy to help you with your query

    If you are having trouble connecting to an external server using a ShrewSoft VPN from an Azure Windows machine, there are a few potential causes. First, you should make sure that the server is reachable from the machine, and that the correct ports are open. Additionally, you should ensure that the ShrewSoft VPN client is configured correctly and that the encryption settings are compatible with the server. Additionally, you may need to configure the Windows Firewall to allow VPN traffic. Finally, you should make sure that the virtual network in Azure is configured correctly and that the subnet routing is set up correctly.

    If the reply was helpful, please don’t forget to upvote or accept as answer, thank you.

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  2. msrini-MSFT 9,261 Reputation points Microsoft Employee
    2023-02-19T09:23:27.2633333+00:00

    Hi, From a VM's perspective there is. Firewall from guest os level and one on Azure which is Network Security rule. You will need to make sure that you allow inbound ports which is required to form the tunnel from your peer IP. Once done check if your peer is reachable by using any layer 4 connectivity tools like psping or nc or tcping.

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