[obombration]

At work, it's probably JIRA. Tons of UI noise, text markup isn't what I expect it to be and nobody around here can seem to agree on what features should be used for a particular scenario.

Past work, it would have been Identity Finder by a landslide. Awful UI, awful support, super intrusive, a total pain to administer, just bleh. Glad I was able to wash my hands of that.

Personal stuff, iTunes. I genuinely like the interface (at least on macOS) but it's huge and bloated and doesn't do some of the things I want it to. If they ripped out everything that wasn't related to listening to your personal (local) music library, I'd probably like it quite a bit. I wish it would write metadata to file tags rather than its own database, but I forgo that if it got rid of all the other crap.

[Mandatum]

JIRA definitely comes down to implementation and policy. I've used it in places and it has been amazingly helpful as a developer, to the point I don't know how we did anything before it.. Then going to a place that totally misuses it and causes me to triple-handle everything.

If your company is large and you're looking at JIRA, pay a consultant to come in, set it up for your different teams and train people. It's worth the money, otherwise you won't see the benefit JIRA brings.

[iLemming]

JIRA. OMG. It's really awful. Its UI is cluttered and inconsistent. Search is slow. It's impossible to find things. Markup syntax is horrendous. It's easy to make mistakes and extremely difficult to fix them.

[jakebasile]

Re: iTunes, I would love a separate Apple Music app for desktop. 95% of the time I open iTunes on desktop it's just to play music. It's cluttered with so much stuff I rarely or never use.

[kyriakos]

Problem with jira is that there's always multiple ways of doing something and the quickest ones are the least obvious ones.