Encrypting your SQL Server’s TDS connections should be high on your list of things to do if you’re concerned with the privacy of your data. This often boils down to one big problem: can you get a valid certificate without paying a ton of money, and will it work with SQL Server?
So follow me down the rabbit hole, as we work out the steps to using Let’s Encrypt to create (and auto-renew!) a certificate for SQL Server. This is going to get technical.