MSSQL SSL/TLS Certificate Chain Fix

I was configuring VMware App Volumes and ran into an issue where the installer reported a MS SQL security alert. Since I am trying to get this to work in a production-like environment, I did not want to just “Trust server certificate” and move along. I wanted this to be installed appropriately. A couple minutes Googling and this post is a record of my findings for the future. Hopefully, it may help you as well if you stumbled here. Here is a screenshot of the security alert.

First of all, make sure you have a CA-signed certificate loaded in the Personal store on the server hosting your MS SQL Server. You can quickly check your machine certificates by clicking the Start button or opening Run and typing certlm.msc. If you don’t have that, stop here and go get one. I used Let’s Encrypt for my certificate.

The next thing you want to do is verify the service account that is running your MS SQL Server. In my case, I am using the default NT Service\MSSQLSERVER.

Right-click on your machine certificate and point to All Tasks, and choose Manage Private Keys…

The Permissions window opens up.

Add the account you verified as the Log On As user when checking the Services.msc management console. (You may need to change the location to the local server name from the Locations… button on the side of the Select Users or Groups window.) Ensure the user has Full Control on the certificate.

Go back to the Services.msc console and restart the SQL Server service and you should no longer have authentication or trust issues with connecting services.

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