On-premise SHIR not connecting through S2S tunnel

Saïd El Kacimi | Analyze 0 Reputation points
2025-03-18T08:49:31.99+00:00

Hello,

I have an issue with the SHIR not connecting through the Site to Site VPN tunnel, I have a private endpoint and a private DNS Zone for Synapse in Azure set up, I have added the DNS entry in the host file of the SHIR machine. The Machine can find the the endpoint with it's private ip when I use nslookup. The machine only connects to Synapse when I allow it to go through the public internet. Does anyone know what I am missing?

(This is my first post here so if I am not providing the necessary information or the right question I am sorry about that).

Azure VPN Gateway
Azure VPN Gateway
An Azure service that enables the connection of on-premises networks to Azure through site-to-site virtual private networks.
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  1. Praveen Bandaru 2,665 Reputation points Microsoft External Staff
    2025-03-18T12:06:37.7633333+00:00

    Hello Saïd El Kacimi | Analyze

    Greetings!

    I understand that you are facing a resolution issue, while are you enabling the public connectivity it is working as expected.

    For further investigation, please provide the following information:

    Could you share a screenshot of the Nslookup from your source machine?

    Also, let me know which DNS you are using in the private endpoint VNET - Azure provided or custom DNS.

    • If you are using custom DNS, you need to set a forwarder in the custom DNS server machine point to azure DNS IP (168.63.129.16.). And also, please confirm whether the custom DNS and private endpoint are in the same VNET or different VNETs, and check in the private DNS zone VNET's are linked properly.
    • If you are connecting from on-premises, you need to configure a conditional forwarder in the on-prem DNS server machine to point to the private DNS resolver. Additionally, you need to configure the private DNS resolver inside Azure.

    kindly check the below document for more understanding:

    https://github.com/msrini-MSFT/Troubleshooting-Private-Link-DNS-Scenarios?tab=readme-ov-file#scenario-2---if-your-source-machine-is-deployed-on-premises-other-cloud


    Hope the above answer helps! Please let us know do you have any further queries.

    Please do consider to “up-vote” wherever the information provided helps you, this can be beneficial to other community members.

    1 person found this answer helpful.

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