It's actually worse than that: Microsoft gives you free integrated desktop virtualization (MED-V) and, in IE 11 they added an Enterprise Mode which works very well with antique sites. Both can be seamlessly integrated using group policy so a user clicks on the blue e, uses the web as normal and when they hit http://creaky-internal-app.example.com the experience seamlessly jumps back a decade.

This isn't being conservative about upgrades. This about an IT department refusing to learn to do anything they weren't doing in 2000.