Cisco ACI. What a janky, buggy mess. Dozens of clicks to accomplish tasks you used to be able to do in less than 5 seconds from the CLI. And the GUI is laid out like a fever dream. You need to script everything to be even close to efficient, even unique one off tasks, and then you spend more time editing scripts than it used to take to do jobs manually from the CLI. We have one environment with a couple hundred independently managed switches that one guy can manage pretty effectively with little to no automation. It takes a dozen people to manage an environment with about three hundred switches and they are always fixing stupid bugs. The staff turnover there is hilarious. Most people try it for a while and then run for the hills.
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Amazon Chime.
I supported a couple dental offices for a while, and I hope I never have to touch EagleSoft again....
CET Designer with in house tools added. Nothing worked well, or even worked as documented for longer than a couple months. And engineering projects using it would last years... We'd go to do as builts and nothing worked the way it did when the project began.
QuickBooks, by far. Running that on premise (which we did before they offered it as a service) was an absolute pain.
Most people wouldn't know about the tool but the ECO suite of tools for ISPs to manage devices is shit (unless they rewrote it since I last worked on it). Companies paid millions in licensing and the damn thing barely worked. It could take two hours to install despite being bundled as an RPM. Code was also a mess of overrides and black magic techniques that made it near impossible to trace and test. And I just remembered the UI was written in Java and it was source controlled by SVN.
Groupwise. What an ugly, barely functional piece of crap. I'd set notifications for recurring tasks and sometimes it would remind me and then randomly stop for a while. Sending email felt like the early days of AOL. I left for about a year and when I came back, they'd switched to Outlook, which I don't love, but it's miles better than what we had.
The job I worked at for that year had a custom Salesforce thing that made me want to find whoever built it and throw something at them. It was supposed to track what benefits clients were receiving, like SNAP, disability, etc, but it was borderline impossible to read, case notes would cut off, and searches would routinely just not work. It soured me on Salesforce permanently if that's the kind of garbage they're releasing.
Outlook mail server in 1999.
Only used for 2 weeks while doing some Y2K relief on site.
Eeeeewww. Felt gross after.
For context, I was using Exim4 at home at the time.
Sorry but FreeCAD, it's just not made for professional use. I don't blame it, I blame my boss for being so tight he had us on Linux cos of that and then plus wouldn't buy me a CAD program.
Back then Web based options like Onshape didn't exist so there wasn't much else..
Startup life for you...
Clearcase and Clearquest. Fortunately we didn't use it for very long.
Adobe Experience Manager aka Adobe Designer. Unfortunately I still have to use it occasionally at my current job.
At my last job we used a proprietary rapid application development tool to do .. everything. It had been used for decades and it’s basically a designer window like Microsoft’s asp net stuff and pseudo code in the background for multi Plattform Desktops and web Applications. The rad in itself is okay: it is written in c++, reasonably fast and has node and js integrations. Buut as said the tool had been used for decades without major refactorings or rewrites or what not. So the codebase was a mix of awful ( you can name variables if so if if is possible ) and straight up outdated. I’d regularly find „commit-comments“ (the integrated vcs is also shit) written before I was born. It was a pain to work with. And we never used the js or node integrations since the new dev lead didn’t know much about developing outside of in said tool which made everything more complicated. So I’m kinda happy to work with js now.