What software you consider so bad it made you happy when you left your job?
What software you consider so bad it made you happy when you left your job?
I've worked with some pretty rotten software, but management software is easily the most user unfriendly, so my vote goes to HPSM.
I didn't leave the job, but I had my resignation letter written over this since I would have had to maintain it:
My former boss had an absolute hard-on for "AI" and brought in this low-bid, fly-by-night "AI" software to automate all of our processes. I'm a fan of automation in general, but not this.
This "solution" was basically a glorified macro generator that would screen scrape data from our apps and key into our other apps. Not only it was built on the absolute shakiest platform imaginable, but the documentation from the vendor outright told you to setup remote desktop services in a way that was in violation of licensing in order for it to work. The stack it ran on made a Rube Goldberg machine look like sleek, fine engineering.
I repeatedly told him this was bad software, but he persisted to the point where we nearly went to production with it.
The worst part? The applications he was screen-scraping were all internally-developed. We had access to the backend, frontend, everything. Rather than writing proper processes, he threw that piece of garbage at it.
Luckily he retired before it went to production, and the new CTO shut it the fuck down.
So, I didn't quit my job over it, but I was looking and had my resignation letter written.
Due to really dumb requirements we had an app that used Python, Visual basic, C and C++, MATLAB, R and JavaScript. I'm not describing an application stack. This was a single binary. The amalgamation was so disturbing that it couldn't even shut down once run, instead asking the operating system to please, please kill me.
Part of the installation procedure involves disabling all SSL certificate verification on company machines.
I’m a camera operator. I work with different cameras on every movie set. The Sony cameras are known to have the worst menu system of all. It’s extremely dense, organized in a manner that makes no sense when on set (the frequently used options are buried in sub menus) and the navigation is painful with a crappy clicky roller. Even the sales rep for Sony openly apologized for the menus. This is unacceptable for a $52,000.00 camera. On the opposite side, there’s ARRI Alexa which has the simplest menu of all. Just a few pages of organized items with simple names. And a lot of common options accessible on the main screen.
Edit:
here’s the Sony Venice menu simulator
And here is the ARRI Alexa menu simulator.
The differences may not be apparent on the simulator but they become critical when on set with a time constraint.
Jira. In the Software-as-a-Service world, it's often the tool of choice by Product teams to track issues, by breaking everything down into stories.
It's a horrible, slow, janky mess. The interface is confusing and poorly laid out, you can easily have too many options all over the place, and how its even used can vary dramatically from one company to another.
Salesforce is also trash for very similar reasons. How Sales people around the world all vouched for this thing is beyond me.
I left a job over MacOS.
The management was bad. The product was bad. I would have left eventually anyway.
But the constant frustration of using a window manager that does not let you make keyboard shortcuts for most basic window operations, like cycling through windows on the current virtual desktop was too much. And MacOS really does not like you to have multiple monitors in different orientations. There were a whole bunch of other stupid things. I always felt like my computer was fighting me, not working for me.
But on the plus side, it did not have an Ethernet jack, it was really thin so the fans were tiny and made a huge racket, the keyboard sucked to type on, and keys would stop working if a piece of dust with any dimension larger the Plank length got under them.
For all the flak it always gets, can I just say I'm relieved nobody said JIRA yet? I think JIRA is great for what to does, but companies are just bad at setting it up right. Either they go overboard with restrictive processes, or they are unorganized mess, there is no in between. But that's not the software's fault. (Braces for downvotes)
25 yr System Administer who has exited IT: Windows
Doesn't matter what job I'm in, Adobe anything is always trash and their seeming monopoly on digital certificate signing in PDFs is disgusting.
SAP
They were transitioning from Oracle SBMS which was bad enough already but SAP... that thing was a nightmare taking dedicated employees (which we didn't have) to account for the additional time needed to enter and manage data
Fortunately I was able to get out before the full switch over; friends that still work there occasionally message to inform how horrible the place has become
Jira is literally a shiny keychain which keeps PMs distracted and busy enough so that they don't start calling people into a million meetings because they have nothing better to do. It is otherwise completely useless and borderline nonsensical, and any perceived productivity gains from its usage can be attributed directly to keeping superfluous managers away from engineers.
I've been in the industry some time but here are some of my most hated software I've been forced to use:
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IBM Clearcase. Absolutely the worst dogshit source control system ever to exist. Complex, fragile, arcane, slow, network intensive. The company had to employ people fulltime on each of its sites whose only job was creating branches and mirroring repos on other sites. The operational & licensing costs of running it must be insane. Some defenders might claim "but it's so powerful!" or "look how we can create fancy layered views" as if that excuses it for being terrible in the most basic ways. Fixing it must have been intractable because IBM Clearcase eventually produced a faster remote client that talked to a proxy of the view running on a server somewhere. More expense and complexity.
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IBM/Lotus Notes & Domino. Another complex, arcane, slow, unintuitive, frustrating product by IBM (though owned by HCL now). Originally a content management system with an email / calendar with its own terminology and workflows completely divorced from any other email / calendar system in existence. Various iterations attempted to rework the front end to appear more user friendly but it was illusory - click button or two and you were confronted with dialogs that hadn't changed in 30 years.
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Internet Explorer. I've worked in company after company that had some really awful in-house expenses system or clock-in/clock-out or some enterprise junk that NEEDED Internet Explorer and no other browser would do because it was so badly written that it couldn't render properly or it used an ActiveX control.
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HP/Microfocus ALM. Another over-engineered, arcane, unintuitive piece of enterprise software. This time for tracking bugs, features, testing etc. Complicated and slow, heavily dependent on Internet Explorer and other deprecated Microsoft tech.
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Trend antivirus. Almost every corporate antivirus is bad but this one has been the bane of my existence. I write code which does stuff like encryption and compression/decompression and this piece of shit would constantly trigger warnings and delete binaries I was trying to build and develop. When it wasn't interfering with my work, it would just be constantly hogging CPU and slowing down disk activity.
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Enterprise software in general. This crap is sold like Kirby vacuum cleaners - a pushy salesman convinces a clueless CTO to buy junk that can seemingly do everything and a sign contract for $$$. And then this stuff is there FOREVER. Management will ignore complaints and the obvious shortcomings of the system because its paid for and the sunk cost fallacy kicks in.
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Historically, anything that required at least half of an employee to manage.
We're talking SharePoint, exchange, scom, mom. I'll give backup software a pass in general because in the days of tapes, no it's nothing you could do about it but backup exec can f*** right off.
It's a little thing and I still have to use it, but Cisco Jabber is the most annoying piece of software I have ever used.
It should just boot up and make calls, right? Nope.
It constantly changes the audio output settings dynamically and I can't get it to stick to what I want. Oh, we using the desktop monitor speakers this time the laptop booted up?
It fails to keep credentials and I have to reset it at least once a week.
It does not have a user setting to make it stop taking over as the messaging app. We use Teams for that, which is also pretty crappy but not nearly as annoying as Jabber. Apparently there is a way to address this during installation, but our IT support can't get it to work so I have to manually start up Jabber before Teams because the last one takes over.
Plus all of that is for an occasional phone call that tends to be missed because Jabber decided to forget the credentials again. I have reset Jabber more times than I have received a phone call through Jabber.
Oracle and a dozen internally developed tools.
Oracle because I'm not an accountant or bookkeeper, but was forced to do a bunch of those tasks anyway.
The internal tools because, while they were "mission critical", they were buggy as hell and there was only a couple of people nationwide who knew how to fix them (or mitigate the damage) when things went wrong.
Clearcase. Some stone age IBM version control system that predates git.
To ensure there are no conflicts with multiple people working on the same file it relies on locking so only one person can work with the file at a time. Super annoying when people forget to unlock their files after use, which everybody will do.
Very niche. https://en.wikipedia.org/wiki/CityTime_payroll_scandal
NYC GOP Mayor Mike Bloomberg's daughter gifted the City a $65 million boondoggle called 'City Time.' Theoretically, every employee was supposed to scan in with a biometric signature. The software didn't account for things like off site work, shift changes, a 24 hour schedule, etc etc. It would have been simpler just to keep the old paper system and imput everything.
I'm a sysadmin with a background in computer science, so I'll say any fucking enterprise software on the planet. It's all trash and annoying. I'd run Debian every day of the week over Windows or RHEL and the likes.
I never knew how much I love and appreciate open source/free software until I worked in enterprise...
"But VMWare PERFORMS BETTER than Proxmox!". Yeah, with 10 times the chance of making you depressed.
I'm a television technical director and Ross Overdrive is hell on wheels... it's a video production system mostly used by local television stations to
consolodate"automate" their control rooms down to one person. There's three major companies that build systems like this: Sony, GrassValley, and Ross. In my experience GrassValley's Ignite is pretty good, it's stable and gets the job done. Sony's ELC is best, going above and beyond what I need it to do (plus their customer service and tech people are just awesome). Hands down, Ross Overdrive is a pile of garbage. Their physical video switchers are really great (super intuitive and built to last), but the Overdrive automation system itself is just a clunky and uncooperative UI. I've had such a bad experience with their system I've turned down jobs when the place uses Ross Overdrive. Ross's Xpression graphics system (or "Chyron") is also a hot mess. I've heard that if you're using all Ross stuff (video switchers, graphics system, video servers, robotics, etc) it runs smoothly and that may be true, but Christ-on-a-pogo-stick have I had nothing but trouble with their software.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.
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???
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.
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.
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.
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.
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.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.
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.
Mac OS X.
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.
- Service Plus
- Salesforce
- Lotus Notes
I think so many people are institutionalized into Microsoft office suite (especially for outlook mail and calendar) and it is just so RIDICULOUSLY bad - I'd never really appreciated gmail or complimented gsuite until my company was acquired and forced to regularly work in outlook.
I immediately took a 50% productivity hit and even daily success towards regular goals just doesn't feel quite like success anymore because I'm always chasing my tail. Luckily I was already an overachiever, so my diminished workload is still good. Stupid company fucked themself out of a lot of wins for such a small, tone deaf decision.
The simplest way I can say it is that before with gsuite I just never thought about productivity apps - they worked in the background to support me well enough. Now that we're in outlook, I have multiple bad interactions that I have to navigate around every single workday.
Maybe you have heard about a software called Ragtime. It‘s basically a combination of Word and Excel. However, there‘s no option to export any files that can be edited with any other office application, and you can‘t open .xls/.odf etc files with it. Oh, and the best part about it: You can always only undo one action.
Windows
Man, HPSM was trash but christ I'd take it back for a ticketing system over Salesforce in a heartbeat. Trashfire tries to do too much and excels at none of it.
During my statistics graduate degree, there was one course we had to do our data analysis using SAS. I absolutely despise it and refuse to work for any employer that would expect me to use it.
SPSS is also crap - at my current job there were some processes that used it's scripting "language". It was both painful but cathartic to slowly rewrite those processes into R.
Micros cash register software. Endless lines of corrupted database entries.
It was legal software called Needles. The firm didn't use email to communicate. They sent Needles messages. I quit after a week.
I had a gig as a software developer at a company that tried to organize its software development with... the most horrid call center ticketing system I've ever seen.
The software was named "TANSS" (an acronym for "transaction action notification solution system" which... says a lot... in a certain way). It couldn't handle UTF-8 and the company had Asian customers, it placed the signature of a different company under each message sent to a customer and project management might as well have been non-existent (supposedly the crapper of a ticketing system had "projects" but it was just a super naive lining up of tasks without buffer times, burndown/velocity chart or anything).
The expensive p.o.s. was strong-armed into the company, probably because one of the company owners had a background in tech support crap where you're generally chasing billable minutes.
I don't know if it was unprofessional by me, but I quickly refused to interact with the whole thing and handed in my notice (and I had actually liked the company and my tasks up until that point). Even Jira, which many consider a highly unpleasant system to work with, felt lean, responsive and fun after that experience.
It's been over 6 years, but I can state with certainty, if I see that system in use anywhere, my respect is gone and whether customer or employer, they'll be a hot potato in my hands form that moment on :)
Salesforce Marketing Cloud.
It was bad at my old job but I thought I figured out a good workflow. Then I switched to my current role thinking they would use it better, it's just introduced new problems for me.
There's all the regular jank of Marketing Cloud that comes from a bunch of poorly integrated acquisitions. But the worst part for me is trying to pass data from Marketing Cloud to Salesforce.
Data just doesn't go through if it doesn't match perfectly. And neither program tells you because it's between systems.
You can fulfil all of Marketing Cloud's requirements, but nothing will happen if things don't match up on the Salesforce end.
Testing a recent campaign was so stressful I've updated my resume and jumped back on the job sites
Amazon Chime.
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.
My company decided to replace selenium with their own in house solution... It didn't work but they kept doubling down on it and tried to present it to all other branches in the org to get them all to buy in. After I left my friend told me it became a dumpster fire and everyone abandoned the project.
Haven't left the company yet but changed department mostly because of Enovia V6. Piece of crap software held together by a bit of spit.
VII, aka V 2, not 7. Just that naming gives you an idea of how unintuitive everything was.
I supported a couple dental offices for a while, and I hope I never have to touch EagleSoft again....
I worked for a company that manufactured products and had been running on NetSuite as the ERP for about a decade when I got there. It had been customized and tweaked and worked pretty well for what we did over that time frame, with lots of time-saving automation. Shortly before I joined the company they were bought by a conglomerate and merged into a division with a couple other somewhat complimentary companies in the central US and west coast. Although it was supposed to be a merger of equals, it soon became apparent the west coast company had won the merger and was calling the shots. They were closer to our largest customer base and while our revenues were pretty similar, they shipped much smaller volumes and had much higher margins (they apparently at one point had a box that just had a Raspberry Pi or something similar inside that they sold for $5k/each). The big difference was we were a big name in a market with a lot of competition, so we had to be efficient and smart with our margins, while they were only big in markets where they had no competition; where they had competition they were often the last choice. While the plan was originally to move everyone to NetSuite, which already had options to run multiple companies/subsidiaries out of one instance, that was abruptly cancelled and we were told we would instead need to switch to Xtuple.
Xtuple was awful. NetSuite runs in a web browser but Xtuple opens multiple windows that look like something written in Java in the late ’90s. Want to copy some text? Unless it’s in an editable text field you can basically forget about it, and even if that field was once editable, many of them can never be edited again after the first time you save, or sometimes even as soon as you click out of it after your first time typing in it.
I don’t even know how much of it was Xtuple’s fault versus the company’s customizations. Where switching to NetSuite would’ve put all the companies in the same instance and allowed for one store to sell all the products, the plan to switch to Xtuple meant a separate server for each company, plus a fourth server to coordinate with each location. When you license Xtuple, you also get access to the source code and can make changes as needed. There was one guy at the west coast company who had total control of the software and no one else had access to it. It seemed like he used this opportunity to create the proverbial million lines of undocumented spaghetti code and guarantee job security. To try and help him with creating all the different Xtuple servers, they hired a consultant directly from Xtuple to create our instance, but when the spaghetti code guy came to integrate it with his part none of it worked, apparently because spaghetti code guy was doing all sorts of things in a non-standard way. This delayed our launch by 3 months because spaghetti code guy then went and rewrote the stuff the consultant did to make it work, and of course a lot of things still didn’t work right for several months after we launched.
Because Xtuple didn’t do everything NetSuite did, some functions were moved to outside software, like Customer/Technical Support to Zendesk. The built-in tools in NetSuite weren’t the best, but it was directly integrated so it pulled customer and product history in and could make an RMA directly in the ERP, so when the product arrived Receiving basically just had to push a button to check it in (the west coast company had never bothered putting their repairs in Xtuple much beyond listing the final price of the repair; they managed the actual repair process in a massive, unwieldy Google spreadsheet). Zendesk didn’t have that, so all of the data had to be manually entered twice, once in Zendesk, then again in Xtuple. We also didn’t put our old customer history into Xtuple, including even just a customer list, partly because the west coast company assured us they already had all the same customers as us (it turned out they maybe had a third of our customers, and that only counts business customers, not individuals). Since we had access to the code it seems like we should’ve been able to tie directly into Xtuple, but spaghetti code guy would only allow custom APIs he created. We never even got that to work because a year or so in the head honchos decided to move to Salesforce instead, so they spent a ton more money trying to make that work. When I left they still weren’t communicating, and people coming in from the conglomerate were starting to ask why millions of dollars had been spent on multiple transitions to rebuild functionality that still wasn’t working 3 years in. They were also cancelling the 4th Xtuple server to control the other 3 because they just couldn’t seem to make it work.
In the end there are a lot of things I don’t miss from that company, but I found Xtuple to be especially x-stupid. Still, I don’t know if it was the software itself or spaghetti code guy. Everyone acknowledged he was a problem when he wasn’t in the room, except maybe the CFO, but no one could do anything about it because it seemed like the businesses would completely halt without him.
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.
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.
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.
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.
Adobe Experience Manager aka Adobe Designer. Unfortunately I still have to use it occasionally at my current job.
3DS MAX, Zbrush
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.
"ORION" - UPS , I'm not dying over it. It is supposed to give you the most "efficient" or shortest route. Worst part is they forced us to follow it. Thats when I knew to quit.
Clearcase and Clearquest. Fortunately we didn't use it for very long.
I have plenty of stories from when I used to work in purchase ledger and customer service.
Klick2Contact is the biggest piece of shit I've ever used. Imagine a CRM that randomly crashes and loses your tickets, and where it can take several minutes to assign an email to yourself. Now imagine having to use software that bad whilst logging cases on a separate CRM (because K2C wasn't fit for purpose) and answering emails within a 10 minute SLA.
Best I used in terms of call centre software was Salesforce. Ironically it's not specifically designed as a CRM.
Part of the reason I got fired from my old call centre job was trying to deal with K2C.
Worst enterprise level accountancy software I used was probably a tie between JD Edwards and OpenAccounts. Best accounting software was definitely Xero.
Oh man im not sure if i hate HPSM more or the in house dumpster fire my corp replaced it with
I work in manufacturing and haven't left yet so I still suffer, but my God will I be so happy to leave Visibility behind...
What an absolute nightmare, shit system... 2 years in and we're still suffering every day from it. No one here likes it at all.
IBM Websphere and Eclipse. What a horrible way to develop a application.
Windows server and all the half-working crap it comes with it. I ended up replacing most functionalities with third party tools because Microsoft doesn't know about good UX. OS deployment? Replaced, GPO? Replaced where possible. Patch management? Replaced.
Anyone ever use Accela?
Autodesk Maya 2016
Oh man, outlook? Mostly just because I hate email. Or slack because I hate people being able to just grab my attention from what I'm working on.
Right now, I'm getting super fed up with SCVMM. I'm used to vcenter and having to migrate everything last minute to hyper-v keeps showing me why I've always gone VMware for everything. It's just a clunky, unoptimized UI, giving me cryptic errors with surprisingly little online documentation. I feel like Microsoft really, really could do better but they don't want an alternative to Azure so they make it intentionally hard. It's just unoptimized software with too much overhead for a hypervisor.
Getting this deployed and configured is a battle of two steps forward and one step backwards.
Banner.
Jira.
VMware Workspace One.
That shit is so ill suited for management of computers that it's a wonder they ever sold a single license.
Every time I get away from JIRA for a while I praise Hopper.
Verizon Wireless POS. They went through 3 versions while I was there, and each was as bad as the last.
Sungard Apsys.
It's a banking software I used in one of my first jobs for the frontend of a trading & clearing house, and it's the most convoluted and unintuitive UI that I've seen in my entire life.
Note that it might have changed since, I was working with it prior to 2013.
Asana.
Not having to use Teams anymore certainly would.
Aras PLM
Adobe Coldfusion
Pretty much any consumer grade router firmware.
Even the higher end ones designed for gaming or other pro-sumer inference.
Slow, crappy UI, unintuitive, and most of them fail to accept backups made for a different version of firmware. So you spend days tweaking your firmware, adding routing, port forwarding, subnets, fixed IPs and back it all up like you’re supposed to. A firmware update dumps your settings, you expect to be able to restore from backup, and the firmware says nope, cannot backup from previous versions. WTF.
Happened enough times where I now no longer use off the shelf routers anymore. Horrible.
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.
Permanently Deleted
Cova for a dispo
MyRedVest!
Gage Insite, by IndySoft. I don't currently have time to get into it.
Camunda BPM is pretty bad.
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.
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.
Paycor is making me leave my job currently. It's just a mess of weird shit that makes no sense with zero support.
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.