Why Can't My VPN Clients Resolve Azure SQL Private Endpoint to Private IP?

August 14, 2025 1 answer
Asked by CuriousCat42
Hey everyone, I've set up an Azure SQL Database with a Private Endpoint in my VNet, and it's all working perfectly from the VMs within the same network. But, I'm facing an issue when connecting via our Azure route-based VPN. The clients can't resolve the SQL Database to its private IP; it keeps coming up with the public IP instead. Here's a quick rundown of what I've done: - Created a SQL Database private endpoint that's integrated with a Private DNS Zone (privatelink.database.windows.net). - VMs inside the VNet can resolve the private IP and connect just fine. - VPN clients connect through a route-based Azure VPN (Point-to-Site). - I tried setting up a DNS forwarder VM inside Azure to direct privatelink.database.windows.net to 168.63.129.16. - I've flushed my DNS cache, reconnected the VPN, and even rebooted the clients. The issue remains: my VPN clients still resolve the database URL to the public IP instead of the private one. I'm wondering: 1. Is there a DNS setup step I'm missing for the Azure VPN clients to resolve private endpoints? 2. Do I need to link the private DNS zone to the VPN gateway VNet or just the one with the private endpoint? 3. Are there any specific settings needed for route-based VPNs to handle Private Endpoint DNS resolution? Any insights, tips, or examples would be greatly appreciated! Thanks!

Answers

TechWizard99
It sounds like a DNS issue. You'll need a private DNS resolver set up to create a conditional forwarder for the SQL service's FQDN. Just remember that Azureโ€™s built-in DNS can only be queried from within Azure itself. Make sure the DNS forwarder VM uses Azure DNS as the DNS server! Also, definitely check if you've got a conditional forwarder for the whole database.windows.net zone.

CuriousCat42: Thanks for your quick response! Iโ€™ll definitely give that a shot!

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