December 3, 2025 at 3:55 am

A Worker Was Told He Wouldn’t Be Paid During His Vacation Time After His Company Was Sold, So He Royally Screwed Over His Company When It Was Time To Retire

by Matthew Gilligan

man at his desk

Shutterstock/Reddit

Never mess with a worker’s vacation!

Because things can get dicey in a hurry if that happens…

Check out what went down in this story from Reddit’s “Malicious Compliance” page.

Start now!

No vacation? Malicious compliance with IT policy.

“My father had a job as a mainframe operator for a company that had contracts doing work for state governments, involving a lot of data processing.

His job involved babysitting a group of servers and rebooting them when the monitoring software said they hung, occasional minor programming, and annually talking to the auditor the state whose contract he worked on sent in.

This guy was on top of things.

The auditor loved him because he always ensured they had detailed records ready. Also, the contract specified that absolutely everyone on the contract had to be a US citizen, and the auditor always demanded names and social security numbers.

He had about 5 years to go to retirement. (In 2 years he would be eligible to retire, 5 until he maxed out his benefits.) They really desperately needed somebody to take the night shift, so he took it.

This sounded like a decent deal.

He would be allowed to work from home full time, and he would be retiring soon anyway, and he would save a young married family person coworker from having to do it.

Every fall he and I have a week’s vacation together in Disney World, because he owns a timeshare there. One year, almost 3 years into the 5, he showed up looking kind of steamed, so after we checked in I asked him to spill the beans.

It seems that his company had decided to sell off the division, and they were purchased by an outsourcing company in India just the week before.

Hmmm…

The new company told him he’d have to attend some mandatory meetings during our vacation.

When he explained that he had vacation booked for that time and would therefore be unable to attend the meetings, they said “no you don’t, your vacation time was accrued with the old company and they approved the vacation time, you have no accrued vacation time with us, so if you want to take the time it’ll be unpaid and we’ll note in your HR record that you demanded time off without approval.”

He and I already had a few thousand dollars sunk into the vacation, so he said “OK” and took it unpaid.

When he got home, he immediately looked it up, and figured out that if he retired in a few months, instead of waiting 2 more years, he would get about $50 a month less money. He decided that the money was worth it to him, so he started the process.

He tried to tell them…

The new employer instantly hired temps from India to work on the contract. My father pointed out to them that he was responsible for proving to the auditor that only US citizens in the US were working on the project, so the company flew them to the US.

He pointed out to the employer that they still weren’t US citizens, they shrugged, and he figured out that he would be retired before the auditor came around again so they could deal with losing the contract after he left.

He printed copes of his emails to them saying “you can’t do that or you’ll lose the contract” and their emails to him saying they didn’t care what he said, and kept the prints to cover his behind.

Meanwhile the new company announced that he had to have a cell phone. The old employer had skipped that because everybody knew that cell phones don’t work at his house (no coverage from any carrier), but the new company insisted on it.

He had to spend several hours doing paperwork about it, and then they sent him one. It didn’t work, as expected. So they demanded he bring it into the office in person, which ate a couple days of his work time, because he had to get to a day schedule, then spend a day driving it in, then go back to a night schedule.

These people were pretty clueless…

When he drove it in IT looked at it, and of course they found nothing wrong, because there was cell coverage at the office. So IT took that one and they sent him another one. Lather, rinse, repeat.

Then he had to get back on to a day schedule for them to send a technician around to determine where at his house there was acceptable signal so they could install a booster.

This took several days of his work time, and of course, the tech was amazed that there wasn’t any place at his house with any signal at all. They finally sent him a third phone, and he put it in a Ziplock bag and put it aside.

Dad had a Windows XP laptop for work, and the current version was Windows 7. He’s not an “I refuse to upgrade” person, the problem was that the company refused to pay for upgrades to the monitoring software for the mainframes and the version they had would only run on XP.

The IT department for the new company really wanted everyone on 7 and off of XP. He and all his coworkers refused.

What a waste of time and money!

However, since they all worked at the office, they’d come in one morning and find they had a shiny new computer which wouldn’t run any of their software, so they were an entire staff of IT professionals getting paid a salary to twiddle their thumbs.

My dad wasn’t there, so IT couldn’t get their hands on his laptop, and he became the only person who could tell what the servers were doing. IT got increasingly nasty about it, until they finally cut him off the network entirely, and he had to get his boss to intervene.

The time finally came for him to retire. IT had been nagging him several times a day to make an appointment with them on retiring day to give them his laptop and the unused cell phone, and he had to have a “goodbye” meeting with his boss anyway so he was going in instead of mailing things.

When the day rolled around, he went in, and IT met him first, and took the laptop to be wiped and disposed of. Then he met with his boss. They chatted for a while, and then it occurred to the boss that the laptop kinda mattered because it was literally the only computer left in the company with which they could run the vital monitoring software.

Oops!

My dad said “Oh, IT took it from me an hour ago to wipe it.”

The boss actually screamed “NOOOOOOOOOO!!!” and ran out of the room.

My dad waited a while and left. He never saw the boss again.”

Here’s what folks had to say on Reddit.

This person was impressed.

Screenshot 2025 11 20 at 6.24.47 AM A Worker Was Told He Wouldnt Be Paid During His Vacation Time After His Company Was Sold, So He Royally Screwed Over His Company When It Was Time To Retire

Another reader weighed in.

Screenshot 2025 11 20 at 6.24.57 AM A Worker Was Told He Wouldnt Be Paid During His Vacation Time After His Company Was Sold, So He Royally Screwed Over His Company When It Was Time To Retire

This individual shared their thoughts.

Screenshot 2025 11 20 at 6.25.04 AM A Worker Was Told He Wouldnt Be Paid During His Vacation Time After His Company Was Sold, So He Royally Screwed Over His Company When It Was Time To Retire

And another reader had a lot to say.

Screenshot 2025 11 20 at 6.25.32 AM A Worker Was Told He Wouldnt Be Paid During His Vacation Time After His Company Was Sold, So He Royally Screwed Over His Company When It Was Time To Retire

This is what happens when you don’t treat your employees well!

If you liked this post, check out this story about an employee who got revenge on a co-worker who kept grading their work suspiciously low.