How to troubleshoot Azure Data Studio "error occurred during the pre-login handshake" when adding on-prem SQL Server connection?

Question

Azure Data Studio verison 1.35.1 is installed on my MacBook Pro running macOS Monterey version 12.3.1. Here are the steps I took to generate this error.

1. In "Accounts", I added a Windows Server domain level account authenticated via "Azure Active Directory - Universal with MFA support."
2. Then under "Connections", I clicked "Add Connection" to add a new connection to my on-premise SQL Server.
3. Connection Type: Microsoft SQL Server; Server: myDB.servers.myComp.org; Authentication type: Azure Active Directory - Universal with MFA support; Account: [email protected]; The rest of the options I left it blank.
4. I clicked the "Connect" button and below is the error I got.

Microsoft.Data.SqlClient.SqlException (0x80131904): A connection was successfully established with the server, but then an error occurred during the pre-login handshake. (provider: TCP Provider, error: 35 - An internal exception was caught)

I cannot use the "Windows Authentication" drop-down option as my Authentication type in the Connection Details because I'm logged in with my regular account and not a Windows Server domain account that has access to my SQL Server instances. Our SQL Server instances are configured to only allow Windows Server domain level accounts. Our Windows Server are configured to use MFA but our SQL Server instances are not.

Answer 1

Please try by setting "TrustServerCertificate" connection property to "true" on your connection in the advanced properties /to the end of connection string.

1. The reason you might be seeing issue is because you may be missing certificates on TLS handshake process in windows level or internal VPN configuration don't have certificates installed.

2. Also try increasing the connection time out to a little larger value.

   ....Encrypt=True;TrustServerCertificate=True;Connection Timeout=30;

References:

1. azuredatastudio issues(github)
2. azuredatastudio issues

other workarounds:

1. If still facing the issue try by changing Encrypt value from True to False

2. Make sure that TCP/IP is enabled as a client protocol on the application server and in case of issue try upgrading to/enabling TLS 1.2 else to tls 1.0

3. Check the port number to be 1433 and make sure the server name is fully qualified in the connection string.

4. Atlast try changing the server to older version and retry.

Also see Troubleshoot common connection issues

sql server - Can Microsoft SQL Operations Studio be used to access MYSQL database on Mac? - Stack Overflow