I have seen this quite often - especially in the health care industry. A small department level application that does everything the users want it to do - and has been working perfectly fine for them for the past 15 years...
They do not want to go through the process of an upgrade - or the additional cost. You have to commission new servers - purchase new licenses for SQL Server - new licenses for the upgraded application (if it exists) - upgrade costs, etc...
Now - if that new system only provides the same level of service they are getting with the original application, what is the incentive to upgrade? If there are no new features or fixes available - or dramatic performance improvements - or something else...there is absolutely no incentive to upgrade and incur that cost. Upgrading solely because a platform is no longer supported isn't justification for the added expense - unless you can show how it will save the company money.
If the application is vendor supplied and the vendor does not have a new version available - then upgrading SQL Server will require the vendor to certify their application. If the vendor isn't certified to run on the latest OS and latest version of SQL - performing an upgrade not only runs the risk of breaking the application - but also runs the risk of violating the maintenance contract.
On the other hand - if the vendor has new versions available - supported on the latest OS and SQL, and the company has decided not to take those upgrades on a regular basis, then the company runs the risk of being out of support on that application and met with a requirement to upgrade or lose that support. This is one of the reasons to justify forcing an upgrade when that upgrade doesn't actually resolve any known issues with the current version.
All of this has nothing to do with recommending an upgrade or not - it is assumed that IT has already made the recommendation, or the vendor has made the recommendation to upgrade. The question always comes down to whether or not the cost of the upgrade is worth it - in time, money, effort, etc...
Problems are opportunities brilliantly disguised as insurmountable obstacles.
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