What is the worst IT setup you have seen at a company?

My current company has a script that runs and deletes files that haven't been modified for two years. It doesn't take into account any other factors, just modification date. It doesn't aks for confirmation and doesn't even inform the end user about.

Startup in a rented house in a residential neighborhood

“Router” was an old PC running Linux with a few network cards, with no case, with a household fan pointed at it to keep it cool

Loose ethernet cables and little hubs everywhere

Every PC was its own thing and some people were turbo nerds. I had my Linux machine with its vertical monitor; there were many Windows machines, a couple Macs, servers and 2 scrounged Sun workstations also running Linux

No DHCP, pick your own IP and tell the IT guy, which was me, and we’ll set you up. I had a little list in my notebook.

It was great days my friends

We went out of business; no one was shocked

I have posted about this before. I'm pretty sure I win.

I'm not going to name names. I worked for a company, three of their clients include the United States Air Force, the United States army, and the United States Navy. They also have a few thousand other clients, private sector, public, and otherwise. Other nation states services as well.

I worked for this company quite recently, which should make what I'm about to tell you all the more alarming. I worked for them in 2021.

Their databases were ProgressABL. I linked it because if you're younger than me, there's a slim chance in hell you've ever heard of it. I hadn't. And I'm nearing 40.

Their front end was a bunch of copy/pasted JavaScript, horribly obfuscated with no documentation and no comments. Doing way more than is required.

They forced clients to run windows 7, an old version of IE, all clients linked together, to us, in the most hilariously insecure 1990s-ass way imaginable, through tomcat instances running on iis on all their clients machines.

They used a wildcard SSL for all of their clients to transact all information.

That SSL was stored on our local FTP server. We had ports forwarded to the internet at large.

The password for that ftp server was 100% on lists. It was rotated, but all of the were simple as fuck.

I mean, "Spring2021". Literally. And behind that? The key to deobfuscate all traffic for all of our clients!!

The worst part was that we offered clients websites, and that's what I worked on. I had to email people to have them move photos to specific directories to get them to stop failing to load, because I didn't have clearance to the servers where we stored our clients photos.

We had legit secure servers. We used them for photos. We left the keys to the fucking city in the prize room of a maze a 12 year old could solve.

Holy shit.

Coffee shop open WiFi on the same network as the main retail central point of sale system server for several stores.

My current job.

Many SQL servers use scripts that run as domain administrator. With the password hard coded in.

Several of the various servers are very old. W2K, 2003, 2008. SQL server, too.

Several of the users run reports via rdp to the SQL server - logging in as domain admin.

Codebase is a mashup of various dev tools: .net, asp, Java, etc.

Fax server software vendor has been out of business for a decade. Server hardware is 20 years old. Telecom for fax is a channelized PRI carrying POTS - and multiport modem cards.

About a 3rd of the ethernet runs in the office have failed.

Office pcs are static IP. Boss says that's more secure.

We process money to/from the Fed.

My partner worked for a local council. They reset your password every 90 days which prevented you from logging in via the VPN remotely. To fix it you'd call IT and they'll demand you tell them your current password and new password so they can change it themselves on your behalf.

Even worse, requesting a work iphone meant filling out an IT support ticket. So that IT could set up your phone for you, the ticket demanded your work domain username and password, along with your personal apple account username and password.

Permanently Deleted

Saw a mid size clinic where the server was also the personal desktop of the boss - who also used the domain admin user as his main user account. His reasoning was that he needed to see "everything" his employees did and that none must come "above him" IT wise.

And before I forget it:The machine was in his office where he still was seeing patients and where often patients were left unattended - without him locking the machine.

It's it too soon to say, "letting Crowdstrike push updates to all your windows workstations and servers"

We make users change their passwords every 90d. And log them out of their devices once a week. I don't think this adds any security at all. It just reduces productivity (IMO).

Source control relying on 2 folders: dev/test and production. Git was prohibited due to the possibility of seeing the history of who did what. Which made sense in a twisted way since a previous boss used to single out people who made mistakes and harras them

Wells Fargo. I worked for them for a few years and I have never banked with them after witnessing the travesty of inefficiency and incompetence, literally in my face.

I was hired to implement a CRM for an insurance company to replace their current system.

Of course no documentation or functional requirements where provided, so part of the task was to reverse engineer the current CRM.

After a couple of hours trying to find some type of backend code on the server, I discovered the bizarre truth: every bit of business logic was implemented in Stored Procedures and Triggers on a MSSQL database. There were no frontend code either on the server, users have some ActiveX controls installed locally that accessed the DB.

I had a boss at an animation company (so not exactly a hub of IT experts, but still) who I witnessed do the following:

• Boot up the computer on her desk, which was a Mac

• Once it had booted, she then launched Windows inside a VM inside the Mac

• Once booted into that, she then loaded Outlook inside the Windows VM and that was how she checked her email.

As far as I could ascertain, at some point she'd had a Windows PC with Outlook that was all set up how she liked it. The whole office then at some point switched over to Macs for whatever reason and some lunatic had come up with this as a solution so she wouldn't have to learn a new email thing.

When I tried to gently enquire as to why she didn't just install Outlook for Mac I was told I was being unhelpful so I just left it alone lol. But I still think about it sometimes.

Using Filezilla FTP client for production releases in 2024 hit me hard

A company making signage and signal lights for road construction, with 15 employees. Their former IT guy had switched all of their PC's to Linux for ideological reasons and to save money.
Then they found out that they had a long term contract for an accounting software that housed all their customer and billing data, only ran on Windows and required a server-client model.

So they hauled in the boss's private laptop which ran Windows 7, and installed both the server role, database and client software on it. When his employees needed to access the accounting software, the boss had to stop what he was doing and grant them full access to his laptop via teamviewer. When the boss's laptop was off or he was on vacation, there was no way to access any price info, customer contact info, or financial data (This was during Covid when everyone was working from home).

The laptop was set up to back up (using Windows 7's integrated backup tool) to an external drive which wasn't attached and no one remembered ever existing.

The Linux server (which was actually a gaming PC) was running and attached to an MCU when my company surveyed their infrastructure, but no one (including the former IT guy) knew the correct root password, and we never found out what it was even doing.

One of my ex employers sold a construction company a six figure "building logistics system" which was just a Microsoft Access file. And the construction dudes had to use a CDMA dongle to remote desktop into a mainframe to open their access files. A travesty.

Freight shipping company still running on a custom AS400 application for dispatch. Time is stored as a 4-digit number, which means the nightside dispachers have their own mini Y2K bug to deal with every midnight.

On one hand, hooray for computer-enforced fucking-off every night. On the other hand, the only people who could fix an entry stuck in the system because of this were on dayside.

Apparently, this actually isn't uncommon in the industry, which I think is probably the worst part to me.

I was a backend developer for a startup company where:

• Windows servers without any firewall and security hardening.
• Docker swarm without WSL. We had to use 4 GB Windows base images for 50MB web apps.
• MSSQL without any replication and backups.
• Redis installed on Windows via 3rd-party tool that looked like a 2010 era keygen generator.
• A malware exploited the Redis * what a surprise * and kept killing processes to mine crypto on CPU...
• VPS provider forgot to activate new Windows Server on production and it kept restart for every 30 minutes until I checked the logs and notified them about the missing license.

I left there after 6 months.

A behavioral health company with 25 iPads deployed to field employees as patient data collection devices all signed into the same iCloud account instead of using MDM or anything.

They all had the same screen lock PINs and though most of the data was stored in a cloud based service protected by a login, that app's password was saved by default.

This was 5 years ago at a usd200mil multinational...

The email system was pop3. There were no document backups. There was no collaboration tools. There was no IT security. You could basically copy company data out and no one would ever find out. The MS Office license was bought singly. Ahem!

No IT at all.

I started a job at a university department. A previous admin had a habit of re-purposing desktop machines as servers. There were at least a dozen of them. The authentication server for the whole department was on an old Dell desktop. All of the partitions were LVM volumes, and the volume group consisted of 3 physical volumes: The internal SATA drive, a bare SATA drive in an external USB cradle, and an external USB SSD.

This is why we drink.

Probably not as bad as some of the other examples here, but the company I currently work for has its 10tb shared drives backing up to a server that’s right next to it in the same cabinet. Those two servers, plus all of the networking hardware and a variety of ancillary devices are all plugged in to one socket via a bunch of extension cords.

Yes, the boss has been told to get it sorted, but he’s the kind of older guy who doesn’t give a shit.

This want their fault and I feel for them.

Working in telecommunications and we get a call from a customer that they are moving premises in 3 months time. They want us to check the place out of we can get a service in there. All goes well, time table for install goes out and we rock up the day after they get the keys, only to find the previous tenant took ALL the copper cables with them. Now when I say all, I mean ALL. Data, telephony, and power were stripped out all the way back to the dmarc point of the building.

They were fucking pissed. The lease for the existing place ran out about 3 weeks after the got the keys to the new place.

Current company (Remote Desktop inception): Linux host machine -> Remote Desktop to windows machine -> Remote Desktop to Linux machine

Bad frame rates, modifier keys hardly ever work, super annoying to code. Windows machine resets all settings and files (besides desktop and one specific folder) each day. Each day I have to install a language pack, change display options, keyboard layout etc.

An IBM PC portable. Yes, PC. 4.77MHz, 256k RAM, two floppy drives. Built-in a maybe 8" green CRT screen, and the keyboard could be used as cover for the screen and disk drives.

In theory, this thing was portable. If you were a body builder. The case was steel, and the whole beast was about 15 to 20 kilograms.

I have worked as a lead developer for a major print shop with about 100 employees. The entire order workflow for all branches was shoehorned into one order management system that was initially hacked together for one or two users. It was built on a then already ancient OpenERP system and it had a PHP and smarty frontend for the actual order management. All was hosted on one old debian box which was a VM on a Windows server.

At some point in time, MT decided to slap a web shop onto this system, which was part of the main code base. User data were saved into the same database with plain text passwords. That was convenient for the support people: if somebody forgot their password, you could call support and they would read you your password over the phone.

Another thing that made my hair raise in fear, was that for every single order, any working file was retained indefinitely, even in the light of the then-looming GDPR laws. This amounted of terabytes of data, much of it very private.

I worked at the main branch. When a person walked in, there was a desktop computer at the counter. No password protection, an order management screen open by default. People could just walk in and start viewing orders at will. I am not sure whether they did, but we did push MT to at least have manadatory password protection on their PCs.

Windows

*shudders and goes to take a bath*

My coworkers and I have to remap the network drives to our office wide file systems 2-3 times a day to access the files. This is the main file storage(some teams have moved some stuff to google drive but that doesn’t work for sensitive info).

I know it's a bit of a silly example, but in the public school in Korea where I taught for a while, teachers would write their Windows passwords on post-its and stick them to the monitors. Haha!

The IT guy wasn't really an IT guy.

Office Depot. They are still using IBM machines from the 90s with receipt printers the size of a shoebox.

All Macs

The recent Falcon cock up?

IBM

/thread

One of the worst IT setups I’ve encountered involved a company using a patchwork of outdated systems and manual processes. They had multiple disconnected applications for different functions—some were on-premises and others were in the cloud, with no integration between them. This led to data silos, inconsistent information, and a lot of manual data entry.

After researching for months, finally the company adopted an ERP system which has greatly improved their situation. This system eliminated the need for manual entry, reduced errors, and provided a centralized view of their operations, leading to better decision-making and efficiency.