Quickbooks. Intuit can be burned to the ground.

LibreOffice Calc.

Pro is that my company is very pro-linux.

Con is that calc is so broken. At first, I thought it was just me. But even our accountants were quietly building spreadsheets in Google Sheets and then "pretending" like they use Calc.

We had one application we used (that got retired two years ago) where Control-C had been mapped to bring up a calendar.

There was no need for a calendar in the application. It didn't enable other features or anything that I could tell.

But the software was also woefully out-of-date. They'd decided not to pay for the updated version.

Was quite happy to leave Lotus Notes behind. Will be almost as happy to leave MS Dynamics 365 behind at some future point.

The Foreman/Red Hat Satellite. Many people wont know what it is, but it's the worst, bugiest, slowest piece of garbage I've ever touched.

Also Windows... I'm a Linux sysadmin but my work computer "needs" to use Windows and I've never disliked it as much as when I've been forced to work with it. Why is the virtual desktop experience so trash???

Moodle.

Trying to turn it into an enterprise level LMS without paying any money was an interesting nightmare.

In-house "temporary" assembly line monitor written in Object Pascal around 2006, mostly unchanged since, too badly written to be used effectively, but too mission-critical to risk downtime with a potential fix/replacement.

Oracle DB

Maybe a bit niche, but the Scanco software for computed tomography analysis. Cant remember what it’s called off the top of my head. It’s horribly dated and unintuitive. It does work though! My favorite was when we stopped being able to use it for several weeks, we thought it was busted. We contacted the company for help and they informed us that with a new update the numlock key toggled a “feature” that prevented editing files. No visual representation that editing was locked. Wild

Asana is a laggy piece of shit on any hardware with any internet connection if the board is big enough. And they are usually big.

Anything related to XCode is a fucking nightmare.

Custom made software for controlling electro -plating factory.

It runned on 2 win10 machines, used some combination of excel and proper database software. Multiple people needed to have access, so remote access tool ...

So basically they added multiple features in 10 years and by the time I worked there it was a mess.

Microsoft dynamics AX.

Mac OS and R

Not a job, but I was happy to stop using Blackboard when I left community college lmao.

Carbon Black. As a software developer, running unknown/untrusted binaries is kind of a big part of my job. We also had a MITM SSL-intercepting proxy which made my life miserable, especially when dealing with Docker containers. I actually ended up patching Docker to automatically inject the certificates and proxy environment variables.

On the plus side I learned a lot about certificate errors which has made me the go-to guy for any SSL issues in my current job.

The programming language Java. I could rant for half a goddamn hour.

Oh, and Tivoli Storage Manager/IBM Storage Protection. What a fucking garbage "data protection" application. Fucker couldn't even give me a reliable system state restore in modern OSs.

My company got acquired by a competitor, we had been running on PeopleSoft, and I don't remember the software the new company used but it was a soul sucking black screen with basically a DOS prompt that you had to learn key combinations to use. I had never thought I cared about the beautiful visual interface of PeopleSoft but my God it turned out I did.

• Service Plus
• Salesforce
• Lotus Notes

Still at the job, but QuarkXPress is such immense garbage and most of our legacy documents were built in it so It still a daily requirement, thankfully InDesign was an option for use a few years after starting so its less of an issue these days. Obviously no piece of software is perfect but the amount of extra steps Quark causes to do basic functions reminds me of back in college when I was forced to use Avid for some class projects—similarly bloated, clunky, unintuitive nonsense.

Quark touted adding the “eyedropper tool” a few years back in a new release—in 2020 (or maybe the 2019 version, I can’t remember). This software is just as old as InDesign, the fact they didn’t add an EYEDROPPER tool for style selection is beyond confounding. They also hadn’t implemented individual cell styling for tables until like 2018. The company also has the nerve to put front-and-center that it will open and convert InDesign files in an attempt to appeal to people sick of Adobe’s current subscription model (which don’t get me wrong, I am equally annoyed with), but let me tell you as a daily user of both: STAY AS FAR AWAY AS YOU CAN FROM QUARK.

Man, I feel spoiled after reading some of the stories on here, but for me, Solidworks. After being trained on Creo, moving to Solidworks is like Fisher-Price CAD.

Many things I'd gotten used to having a dedicated, robust tool for become having to trick the program into doing what you want it to do. The biggest offender is the drawings package - I swear this has not left the 90s in terms of UX design.

I'm not leaving, but damn I have no love for AS400. The 80s are over, but not when it comes to tracking our production.

I once had to rebuild some legacy code for a digital scoreboard. The code was written in a code mentioned in "Office Space". I think it was called top speed.
Until that day I thought it was a made up language.