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2 Windows Server 2012 VM's on MS Azure and access is via RDP over Azure Point to Site VPN using a client certificate.

I can connect to the VM's fine but I need to connect to SQL Server 2008 R2 which is running on the VM. Connecting now gives me a "cannot generate SSPI context" which I assume is down to my current windows logon not been part of the domain.

I am not able to change the VPN setup to use Username / Password as it always reverts back to certificate.

How can I connect to my instance of SQL ? Can I somehow add the client cert to the sql login ?

Any help would be great.

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It seems like this isn't possible with the Azure P2S VPN. As a workaround, install the Routing and Remote access to one of the VM's with NAT and the user can login using the credentials supplied to the VPN.

But if someone knows different...

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  • You can set-up Point-to-Site VPN w/ cert auth: docs.microsoft.com/en-us/azure/vpn-gateway/… but to use certificate-based authentication for SQL you would need to leverage Azure Active Directory and join the SQL instance to a specific tenant: docs.microsoft.com/en-us/azure/sql-database/… Commented Aug 27, 2019 at 1:40
  • Thanks Mike. The SQL Instance in on a VM and not Azure SQL, can it still be joined ? Commented Aug 28, 2019 at 9:56
  • Yes, SQL Server on an Azure VM is a better solution with VPN than is using Azure SQL Database. Commented Sep 6, 2019 at 16:54

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