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I'm having trouble connecting to SQL servers over an Azure point-to-site VPN.

SQL Standard is running on an Azure VM which is part of an Azure point-to-site VPN. It is a named instance. SQL Express is running on a device which is connected to that same VPN. It is the default instance.

Addresses: VM is 172.16.0.4/20 Device is 10.0.0.4/32

Address scheme: http://puu.sh/67BGB.png

They can RDP into each other so I know they see each other.

SQL Browser, and SQL Agent is running on both. Named Pipes and TCP-IP are enabled. I've disabled both device's firewalls.

Could it be something about the Azure VPN? Anyone done this before?

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Solution:

Ensure both SQL instances are set to mixed mode authentication and have SA login enabled

Reasoning:

The VM was a standard SQL install from Azure and was not set to mixed mode authentication, only windows authentication. Because the devices were not part of the same domain it would not recognize that I could connect

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I see this is an old thread but I recently had this issue and couldn't get a good resolve.

The issue seems to come from the fact that the Azure P2S VPN uses a certificate to login and then any attempts to connect to SQL over the VPN result in a SSPI Context error.

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