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Harness (a SaaS CI/CD solution)
It is mercilessly opinionated, has a shitty licensing model, bad Git integration, unusable pipeline code (way too complex to write by hand, have to use the visual pipeline editor).
It wasn't the primary reason for leaving that particular job, but it was a factor. The more I worked with it, the more I hated it.
VB apps running on IIS is up there; I'm happy to never deal with either again. This was pre-dot-net.
Early 2000s doing tech support in a house-built ticketing+crm system that heavily abused things in JS.
Speaking of tech support, all manner of software mentioned here already.
I spent a ton of time working in healthcare IT and there's all kinds of janky mess there. One was a house-built Perl script to handle certain things. It was like 15k lines (and before you blame Perl, we had a Java class that was over 30k IIRC). Never allowed to rewrite it because of how mission-critical it was, yet there were still bugs with it. Healthcare IT in the US tends to have lots of jank, especially the small clinics that had to start by doing everything they could with what they had.
I don't want to leave my current job, but they make us all use Mac (Apple Silicon) for software engineering and I hate it. Nothing works the way I expect, it's not consistent between apps, certain ML tools we use won't work on it (mostly because not x86 arch), etc.
Paycor is making me leave my job currently. It's just a mess of weird shit that makes no sense with zero support.
Gage Insite, by IndySoft. I don't currently have time to get into it.
Hangul Word Processor. It had (has?) an updater that would pop up ads in the taskbar. Unfortunately the developer, Hancom, is so in-bed with the Korean government, it's mandatory software in many Korean workplaces. Korean support has gotten much, much better in every other word processor, it's hardly necessary anymore.
Cova for a dispo
MyRedVest!
Oh, oh, oh! I got one not mentioned yet:
ELK.
Well, not the whole of the ELK stack (Elastic, Logstash and Kibana, though the full stack size is much larger nowadays), but their watchers. A watcher is a piece of JSON with some search specifications on when to trigger and send an alert to email/slack/teams/whatever. We're basically abusing it as an alerting system, and generally it works... Fine... Presuming Filebeat actually ingests our logs (which is partially our fault, as there's a fix, but it takes too damn long to drag 3 teams along to implement what needs implementing to fix that problem).
Anyway, the problem is not the watcher itself, even though it is painful (heh) to learn the structure. It's "Painless", the JVM-based scripting language available in a watcher. It's anything but. It is SO painful to write code, inside of a JSON object, making sure everything is exactly as it should be, having to use the DevTools in Kibana to try and trigger it, wait to see what enormous error comes out while praying it works. No IDE, no nothing. Ah, I lied. It does have Syntax Highlighting, for non-Painless code, IIRC...
Oh, having to dig information out of the data you get is super unintuitive too.
At least the UI/Kibana is good, and Elastic is pretty good too. Fuck Filebeat though. And Painless.
