It's certainly not more secure anymore (to answer fistful's question), but all the stuff I was aware of that it was still running on didn't touch the Interwebz.
Not directly at least, but we've encountered malicious logic where it's not supposed to be before.
Not at all because it's more secure. It's a question of the effort of updating the rest of some specialized systems to work with newer stuff.
No truth at all to it being more secure.
The perception is NOT that it's more secure, indeed. The problem is that we have custom software controlling custom equipment, and oddly enough, insufficient money to keep the software updated for the new operating systems.
Consider that the software controls for the F-22 and F-35 have each taken LONGER than microsoft's average operating system lifespans. The planes themselves are not running windows, but ancillary equipment is(and I'm being cautious about naming them). Personally, I recommended using Linux, but hey, I was just a peon.
And that right there is the evil of the Internet age. A software program is a tool, designed to accomplish a task. In the case of a specific, purpose-based program, once you get it up and running so it does what you want it to do and everyone knows how to use it ... why SHOULD it be "upgraded"? I have the carpenter's hammer that my father had when I was born. It was made to drive nails, and it drives nails just as well today as it did 71 years ago. I know how to use it ... what's to be "upgraded"?
As Hawkmoon said. Security. You have a safe from 71 years ago. Will it's systems hold up as well as newer ones up against a safe cracker? Probably not.
The other problem you run into with software is that your needs change. Your father's hammer works fine, sure, but what about when all your competitors have upgraded to pneumatic hammers that let them drive nails faster and with less effort, meaning they can underbid you?
What do you do when you go from needing to maintain 1 house, to 10, to 100? Consider that the population is far higher and far more people have driver's licenses than 100 years ago. Needs change.
But why would a purpose-built state police lookup program need to be "upgraded"? Oh, yeah -- so it'll run on the new IE. Well, why should the state police have to revise their software because Microsoft came out with some new versions of IE? Why isn't IE baclwards-compatible so a program written to run under IE5 will run under IE10?
They 'tried', but the problem is that IE5 wasn't 'standards compliant'. So stuff written to work with it weren't written to be compliant with standards. Think of it like working on a piece of equipment that was built in Africa or something that, for some unknown reason, isn't built using either metric or imperial measurements.
IE5 is no longer supported. That means any vulnerabilities found within aren't fixed anymore. The memory leaks, that you could barely put up with back in the day, are still there. The chips it was designed for is no longer there.
It's a bit like trying to support an antique car - the parts availability just isn't there anymore. Everything gets much more expensive.