Can I upgrade SQL Server 2008 R2 to 2019?

Question

I am creating a web application and want to put it on a server.

I have a server machine that run Windows 2008 R2 Server with a SQL Server 2008 database all set up and ready to use.

Can I put my application on that system or should I upgrade it to Windows 2012 or 2019 server, while also upgrading SQL Server with it?

Note: I was using XAMPP for testing, will SQL Server 2008 be as easy as connecting to PHPmyadmin database in XAMPP?

Answer 1

SQL Server 2019 is not supported on Windows Server 2008 R2, which is in any case heavily out-of-date and insecure.

If you wanted to go with a direct upgrade path for your existing server, you must:

• First upgrade the operating system to Windows Server 2012 R2. You must first upgrade to 2012 R2, as upgrading directly to 2019 or 2022 is not supported.
• Then upgrade SQL Server to 2014, as upgrading directly to 2019 is not supported.
• Then upgrade the operating system to 2019 or 2022.
• Then upgrade SQL Server to 2019.

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Do not do any of the above. As you can see, it's complex, with multiple points of failure.

Just start with a new Windows Server 2022 image, and install SQL Server 2019.

Then do a backup/restore of all your user databases from your SQL Server 2008 R2 to the new machine. Consider updating the compatibilty level, as well as other database-scoped settings.