Scrolling through the top few dozen posts here, I see a bunch of commonly used development software. IMO, all of those do have some issues, but none are remotely comparable to the horror show that is internal software at medium-large corporations. I've used a bunch of these, actually worked on improving a few, witnessed the development process for others. There's no point in naming them, because people outside the company will never use them.
These types of programs are uniquely terrible for reasons described in other posts - the people doing the development, and setting the priorities for development, have no connection to the people who need to use it day to day. Different offices, rare personnel crossover, systems specifically designed to discourage direct communication. They're usually big and complex enough that a ground-up redesign is either impossible, or will inevitably gather enough poor management decisions to be about as bad as before by the time it becomes remotely practical to use.
I recall one place where a critical application required to record data and deliver it to clients in a realtime application was based on an X-Windows application running in Windows XP using the one X-Windows manager that sort of worked there. Yes, really. I know it's a super weird combo, but it's what we had. I ended up moving into a related software department, and got some behind the scenes info. Turned out that there was just one guy left who was still actively coding for it, already past retirement age, but kept on anyways out of desperation, because nobody else was willing to touch that codebase. There was a project to build a more modern replacement application, with all of the usual corporate bloat and ever-slipping deadlines. It wasn't great, but at least it ran natively on Windows 7 and had a better UI. I think they moved over to it entirely after a while, but I left that place before that move was finished.
These types of programs are uniquely terrible for reasons described in other posts - the people doing the development, and setting the priorities for development, have no connection to the people who need to use it day to day. Different offices, rare personnel crossover, systems specifically designed to discourage direct communication. They're usually big and complex enough that a ground-up redesign is either impossible, or will inevitably gather enough poor management decisions to be about as bad as before by the time it becomes remotely practical to use.
I recall one place where a critical application required to record data and deliver it to clients in a realtime application was based on an X-Windows application running in Windows XP using the one X-Windows manager that sort of worked there. Yes, really. I know it's a super weird combo, but it's what we had. I ended up moving into a related software department, and got some behind the scenes info. Turned out that there was just one guy left who was still actively coding for it, already past retirement age, but kept on anyways out of desperation, because nobody else was willing to touch that codebase. There was a project to build a more modern replacement application, with all of the usual corporate bloat and ever-slipping deadlines. It wasn't great, but at least it ran natively on Windows 7 and had a better UI. I think they moved over to it entirely after a while, but I left that place before that move was finished.