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Nearly 20% of Microsoft SQL Servers running have passed end of support
(www.theregister.com)
This is a most excellent place for technology news and articles.
I think in 99% of use cases, upgrading isn't a problem. Most of the time new SQL versions are backward compatible. I've never personally had a problem upgrading a database for a product that expects an older version.
They do have compatibility modes too, but those only go back so far too.
But, I think companies with their production databases for perhaps older complex systems are likely very weary of upgrading their working database. This is most likely where this situation comes from. Imagine being the person responsible for IT, that upgraded the DB server and database to the latest version. Everything seemed to be working fine. Then accounts run their year-end process, it falls over and now there are months of data in the newer version that won't work properly. It'd be an absolute pain to get things working again.
Much safer to leave that SQL 2005 server doing what it does best. :P
It’s not just SQL, it’s frequently the OS. Corporate tools don’t support the new OS so you install the “supported” OS, which is now several years old, and which only supports the next version or two of SQL Server. Microsoft also didn’t help things with 2012R2, which was 2 years later but had the same EOL as 2012.
And yes, you can set compatibility level on the database, but there are still edge cases where the engine version matters. And the business prioritizes, but upgrades are lower on the list than money-making features.