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Boss Told Employee No Time Off During Quarter End, So They Found A Legal Way To Do It

by Leona Pham
November 21, 2025
in Social Issues

It’s not every day that a workplace policy gets used against the very people who created it, but one Redditor did just that when they found a loophole in their company’s PTO rules.

After their boss insisted no one could take time off during quarter-end, but HR emailed that all PTO must be used by the 30th, the Redditor took it upon themselves to dig into the employee handbook. There, they found a clause that stated PTO requests were automatically approved if not denied within 48 business hours.

So, they submitted multiple small requests, watched as they got approved, and took advantage of every minute of PTO, causing chaos within the team and giving HR a headache. Was this a justified use of company policy, or did the Redditor take it too far? Keep reading to see how the community weighs in on this clever act of retaliation.

A worker exploits a loophole in the PTO policy to take time off, despite their manager’s objections

Boss Told Employee No Time Off During Quarter End, So They Found A Legal Way To Do It
not the actual photo

'Boss said I must use my vacation before month end but also “no one can take time off”, so I read the policy?'

Company sends a shiny HR email, subject line all caps, USE IT OR LOSE IT.

We had to burn our remaining PTO by the 30th or it evaporates into the sun.

Same day, my manager announces in standup that due to quarter end “no one can take time off until the 1st.”

I asked how to reconcile that, he shrugs and says talk to HR. HR says talk to your manager.

Cute loop. So I opened the handbook, because I am a petty librarian when annoyed.

Page 14 has this little sentence I never noticed. “PTO requests not explicitly denied in writing within 48 business hours are considered approved.”

There is also a note that partial day PTO is allowed in 1 hour blocks. Thank you, legal team.

I submitted ten separate requests. Two hours every morning next week, two hours every afternoon the week after,

a random Friday 3 to 5 to watch a plumber, and one full day to visit my mom.

I sent the requests in our HR portal, which auto emails the manager and CCs a shared mailbox nobody watches.

Then I went back to my tasks and set reminders. Forty eight business hours pass. No denial.

The portal changes each request to approved, green checkmark, confetti gif.

Monday comes and at 9.58 I put a cheerful note in the team chat. “Heading out, see you at noon.”

Manager pings me to hop on a client call, I reply with a screenshot of the policy and the portal approval. Silence. Then three dots typing, then nothing.

By Wednesday our calendar looked like cheese. Half the team remembered they also had PTO sitting around and started filing it in little blocks.

Meetings kept colliding with green bars. Finance realized that if we did not use the days now, they would be paid out at separation later, which they hate.

HR wrote a new post saying we should “coordinate” but that approvals already granted stand.

My manager called a huddle to ask why productivity dipped. I said we are following HR’s instruction to use PTO. He said he meant in November.

I sent him the original email timestamped this month. He sighed and said he never thought anyone would actually read the handbook.

I used every hour, took my mom to lunch, and my plumber fixed the cursed sink at 3.40 while I drank tea.

Next week a new policy appeared. PTO must be requested in full day increments during quarter end, and managers must respond in 24 hours.

Thanks for clarifying, truly.

Navigating workplace policies can be an exhausting experience, especially when it feels like the rules aren’t designed with employees’ best interests in mind.

In this story, OP is caught in a frustrating loop of company directives and conflicting expectations, leading to a decision that’s as much about reclaiming control as it is about taking deserved time off. While OP’s actions might seem petty to some, they reflect a universal emotional truth: when employees feel powerless, they often seek ways to restore a sense of fairness, even if it means bending the rules.

At the heart of OP’s decision to take action was a deep sense of frustration. In a situation where they were told to use their PTO before the end of the month, only to be told they couldn’t take time off during a critical business period, OP was left feeling trapped. It’s not just about the vacation days, it’s about being respected, being seen.

Psychologically speaking, when people feel like their autonomy is being taken away, it can trigger a need to fight back, to regain control. This often manifests in “malicious compliance,” where an individual follows the rules to the letter, but in a way that highlights the absurdity or injustice of the system.

In this case, OP’s decision to submit multiple separate PTO requests was a calculated move to get what they were due without backing down. While it might have seemed like a small act of defiance, it was deeply rooted in the need for fairness and a sense of personal agency.

According to the glossary on Keka, “When people feel powerless at work, malicious compliance becomes a form of silent resistance.” OP wasn’t simply being petty; they were responding to a sense of emotional injustice.

And when OP’s strategy led to a ripple effect across the team, with others following suit and PTO requests piling up in the calendar, the result was chaotic, but also strangely empowering.

While the company scrambled to adjust, it was clear that this was a moment of collective power, a brief but meaningful reclaiming of control in an environment where employees’ voices had been largely ignored.

In the end, OP’s victory wasn’t just about taking those PTO hours, it was about sending a message that their time mattered. The new policy that followed, mandating PTO requests during quarter-end to be in full-day increments, was a direct response to the disruption caused. Whether it’s a fair or just solution is up for debate, but it’s clear that OP’s action had an impact.

Here’s what people had to say to OP:

This group highlighted the inconsistency in PTO policies

CoderJoe1 − I used to encourage my employees to use all of their vacation time as well as their sick time.

I wanted my team to avoid burning out as it took nearly a year to get a new hire fully trained.

SenorTron − I don't understand what's happening here where at the start it says you would lose the days but then later on says you would get them paid out.

Hoak2017 − This is the manager's equivalent of a developer saying "I never thought anyone would actually use that feature."

These commenters critiqued managers who randomly block PTO usage

Easy_Lengthiness7179 − New policy doesnt address a manager randomly deciding that no one can take PTO that month.

You will be stuck in the same boat in the future, with no loophole to use your time.

hand_me_a_shovel − "He sighed and said he never thought anyone would read the handbook."

Translation: "If I knew you would be prepared I would have tried a different tactic to f__k you all over to make my numbers and nab my bonus."

mallardtheduck − In countries with actual employee rights, denying PTO without an opportunity to use it at

a later date would usually _require_ the company to pay out the time or, if it means you can't take the legally-entitled minimum(*), be flat-out illegal.

Just to be clear; if you don't _have_ to take the legal minimum PTO if you really don't want to

(at least in most countries I'm aware of), but the company cannot _prevent_ you from taking it.

This group shared humorous or insightful perspectives, pointing out how companies often mishandle PTO

Look-Its-a-Name − Ah yes. When manager stupidity meets company policies, the results are always incredible funny.

pacmanwa − Got asked two weeks ago what it would take to cancel or move my vacation. I was going hunting in Montana.

I gave an off the cuff $15,000. "How do you figure?" $1500 for out of state hunting license and tags, $4000 I have to pay the outfitter even if I...

Another $5500+ to reschedule with another outfitter if I do get to go.

I got questioned about the remaining $4000, tips and incidentals and cost of my time to scramble and reschedule everything, and mental anguish.

It had been on the calendar since March. My vacation was not cancelled.

SkwrlTail − I ran into this problem a while back, but also needed to keep productivity.

Solution? Friday became a half day, paid out of the PTO. No other tasks, like cleaning or inventory, I just buckled down and got stuff done.

Result: more productive than a full day, and quite relaxing!

These Redditors discussed quirky or strict PTO systems

AllenKll − 48 business hours? So.... Like a week and a day real time? 48 business hours would be 6 business days. What a weird policy.

NoSwimmers45 − This is why I always make sure my manager knows that PTO for me doesn’t mean “paid time off”

but rather “prepare the others” because I’m informing the company that I will not be present on the scheduled day.

PurpleHippocraticOof − Worked at a place where PTO had to be taken in four-hour increments and sick time in two-hour increments.

And if you were more than 5 minutes late, you had to use either PTO or sick time. You couldn’t just clock in at the 6 minute mark, you had...

Naturally, this turned into people going “ehh traffic sucks and I’m going to be more than 5 minutes late,

so I might as well take a two hour paid break and go to brunch”.

This user critiqued the concept of “unlimited PTO,” calling it a deceptive practice where managers can refuse requests

PunkCPA − This is why evil companies institute "unlimited PTO." It's unlimited in theory, but managers can and do turn down any requests.

No carry over, no final payout, and damned little time off because it's always too busy.

(People getting fed up, quitting, and not being replaced can make the sleepiest workplace busy.)

Was the employee wrong for using the loophole in the PTO policy? And have you ever had to stand up for your rights at work? How did you handle it? Share your thoughts below!

Leona Pham

Leona Pham

Hi, I'm Leona. I'm a writer for Daily Highlight and have had my work published in a variety of other media outlets. I'm also a New York-based author, and am always interested in new opportunities to share my work with the world. When I'm not writing, I enjoy spending time with my family and friends. Thanks for reading!

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