Lovely smell of licenses in the morning...
What nobody seems to realize is how the cost of licensing Windows has increased over the past 10 years.
Say, 10 years ago you set up an Enterprise class W2003 server, installed your application/middleware/database/whatever and it has been running smoothly since then. Except perhaps for the continuous stream of application changes. But the OS has, except for patches, been untouched in 10 years.
Now they have to upgrade and they find that the equivalent "Enterprise" W2012R2 costs... how much more? Good luck and have a good dose of Paracetamol ready for your discussion with your friendly Microsoft reseller, because you're going to find that W2012R2 costs more than W2003 in very subtle and complex ways.
Add that the cost of installing all the upgraded software -because the latest versions are not W2003 certified- the cost of migrating all those customizations to the new version and look at the bill. Twice. Realize that developing the app from scratch will cost you about the same. Take another dose of Paracetamol.
So in a lot of places the result is going to be "Duh, let's move it to a VM, ring fence the network where it is running and call it a day" ... which incidentally will stop the server vendors drooling as they'll discover that their super-duper W2003 hardware with Windows Enterprise is likely underutilized by HW standards of the the current decade.
Security folks will likely show some testimonial reluctance, but after seeing the upgrade bill they'll likely agree that with some mitigations in place they can keep running W2003 until the application is retired. Or forever. Heck, there are some NT4 apps still running out there.
Let's not even start talking about dedicated hardware equipment that depends on W2003 to run.