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Employee Deletes Unapproved Leave Requests From System And Receives Extra Pay For Taken Days Off

by Jeffrey Stone
November 28, 2025
in Social Issues

An office withered into a ghost town as its contract neared its end, the boss vanished without a trace. One worker, having accumulated a stockpile of annual leave, submitted requests to cash out the hours before departing. HR bristled, flooding the system with passive-aggressive rejections, demanding impossible approvals from a nonexistent manager.

Unbowed, the employee persisted, meticulously resubmitting the requests until company policy locked them in: no supervisor approval required to cash out leave upon redundancy. HR’s obstruction backfired spectacularly, granting two weeks of fully paid time off followed by a lump-sum payout for the remaining hours.

HR-directed deletion of unapproved leave yields bonus redundancy payout via policy quirk.

Employee Deletes Unapproved Leave Requests From System And Receives Extra Pay For Taken Days Off
Not the actual photo.

'Remove unapproved leave from the system'

I think it's safe to post this now as the relevant company no longer exists. A few years ago my job was on a 8 year contract that was nearing...

I was looking at redundancy and rather than apply for another job I worked out I was financially better off waiting for HRs axe to fall and take the payoff.

My boss however made other plans, started taking time off and then left.

Admin tasks were being ignored and gradually the offices were becoming empty as people left.

I had a lot of annual leave entitlement banked and decided to book a holiday as redundancy was likely still months away and I used the HR system to book...

I informed anyone who would listen, put in the calendar etc. Of course as my boss was now absent, nobody actually approved my leave in the system.

I enjoyed my time off and came back to work and all was ok. As we approached the final weeks of the contract I had to tidy up loose ends

and asked HR about final payments including any unused holiday entitlement.

What I got back was a snide dig about how I hadn't properly managed my account

as I had unapproved leave requests open that needed to be closed. This was the request for the leave I'd already taken...

So I did what I was told and cancelled the request, adding another 10 days back into my banked leave allowance,

which the HR dept then had to pay me for during redundancy. Thank you very much for the time off and the extra cash.

Ah, the HR system: that gleaming fortress of forms and approvals meant to keep chaos at bay, yet occasionally backfiring like a whoopee cushion under a board meeting chair.

Our Redditor’s saga is A prime exhibit of how rigid protocols in a sinking ship can accidentally reward the rule-follower. With the boss AWOL and the office emptying faster than a fire drill, booking leave via the self-service portal seemed straightforward: notify the survivors, update the calendar, and poof, two weeks of sun-soaked freedom. No formal nod from above? In a ghost town, who’s counting?

Fast-forward to payout time, and HR’s snippy nudge to “remove unapproved leave from the system” flips the script: delete the request, restore the balance, and suddenly those vacation days are back in the coffers, ripe for redundancy riches.

But let’s peel back the layers: was this a sly HR wink or a classic case of the left hand not knowing what the right one’s payroll password is? From one angle, it’s the employee gaming the gaps, spotlighting how automated systems treat “taken but unblessed” leave like a Schrödinger’s cat – neither here nor there until observed (and deleted).

Opposing view? HR might’ve been the unsung hero, quietly engineering a windfall in a company too far gone to care, as echoed in Reddit’s peanut gallery where folks hail it as “HR being a bro for once.”

Zooming out, it’s a snapshot of U.S. vacation payout norms, where the patchwork of state laws turns redundancy into a geographic lottery. According to a World Population Review analysis, in 21 states, like California, Illinois, and Massachusetts, employers must pay out accrued unused vacation upon termination, treating it as earned wages no ifs or buts.

In the other 29 plus D.C., it’s a company policy crapshoot: promise payout, deliver. Go silent, and your beach dreams evaporate without compensation. This divide underscores a national irony where workers leave billions in PTO on the table annually, per estimates from the U.S. Travel Association, fueling quiet resentments that simmer into… well, stories like this.

Enter the experts, HR consultant Alison Green of Ask a Manager puts it in her roundup of workplace tales: “Malicious compliance [is] times when someone purposely exposed the absurdity of a rule by doing exactly what they were told to do.”

Spot-on for our hero, whose delete-key dexterity wasn’t spiteful sabotage but a spotlight on the system’s blind spots, much like the Reddit requesters who flood inboxes to protest micromanagement. Green analyzes these as cultural canaries: not outright rebellion, but a nudge that screams, “Hey, this rule’s got more holes than Swiss cheese.”

Neutral advice: Document everything. Chat openly with HR pre-payout: “Hey, about that unapproved leave, how’s it tallying?” If tensions brew, loop in a neutral third party like an employment advisor for a reality check.

For companies, audit those self-serve portals quarterly. In a contracting crew, retro-approvals could prevent payout surprises.

And for anyone riding out a contract’s final laps? Bank that leave wisely, but remember: the real win is walking away wiser, wallet fuller, and with a story that’ll have friends buying the next round.

Take a look at the comments from fellow users:

Some people believe HR was deliberately helping the employee get extra pay.

curtitch − I know you said the response was snide, but there’s also a chance HR knew what they were doing and wanted to give you that bump.

Some HR folks are absolutely willing to use the company’s policies against it,

especially if they don’t make sense or, in this case, the company was shuttering.

Limakuk − HR knows more about the salary system and the company going down than anyone else.

Besides, they can approve it afterwards, no need to make you remove the request.

They were just being bros making sure you get a little bit more money.

spiteful_rr_dm_TA − That wasnt malicious compliance, that was HR actually being a bro for once and giving you some extra money.

They knew s__t was hitting the fan, and did you a solid by giving you hours back for a cashout.

Airick39 − Hot take. HR was being your bro here. Were they also riding out a contract?

Some people share stories where managers or HR bent rules to give departing employees extra money or benefits.

theVelvetLie − My last position I left at the end of the calendar year. We had a holiday shutdown between Christmas and NYD, but I had given my notice for...

My boss suggested I issue my final day as 1/1 so I could get payout for the shutdown,

but HR didn't like that because policy stated an employee needed to work the day before and day after holidays to be eligible for pay.

She changed my final day in Workday to 1/2, told me to give her my equipment and badge on 12/23

and that she'll return it on 1/2 for me, then wished me well. She was a fantastic manager.

trowzerss − I love redundancies. When I got mine, they had to pay us out an extra month's pay

if they didn't give us adequate notice of the redundancy (I think they had to give us 30 days notice, via official letter).

I still am not sure if our managers were malicious complying us into extra, or if the company decided not to notify us officially to keep more people on board...

but yeah, even though we all knew the redundancy was happening and were actively helping work on the plans,

they didn't notify us officially on paper until the very last day. So really appreciated that extra month's worth of money for free!

Some people share stories of beating a toxic employer at their own game on the way out.

1quirky1 − As the most senior person still present you approved your leave.

As the laziest person still present you didn't put in the effort to properly record your approval.

As the third most corrupt person still present, you erased all evidence of your being paid to not work.

CEO and COO are still doing nothing and getting a golden parachute as they fail up into the next company.

decadenza − OK, have to add mine: A few years back I was an a two year appointment to a IT position at a higher ed institution that's been in...

My appointment was extended until the end of the year after my initial end date. Cool, I'll take that.

Then, expecting that it would again be extended I'm told "no, we (the wealthiest institution) just don't have the money" for the position.

I knew this was double-whammy bulls__t, in that

1) my boss didn't like me because I liked doing things by the book as opposed to "her way", and

2) she figured she'd can me a week (yes one week) before I would be vested in the retirement system.

This meant cheating me out of tens of thousands of dollars. What she didn't know was that

1) my wife (also an employee of said institution) had already found another job at the other end of the state, and

2) I had credited time with said institution from a temporary gig I'd had earlier, meaning

1) I was going to quit anyway, and

2) I was vested and she didn't know it! It was sweet to show my back to that place. Damn, what a toxic atmosphere.

In the end, our Redditor’s delete-button detour proves that even in a company’s swan song, a dash of diligence can harmonize with happenstance for a harmonious (and hefty) finale, transforming a snide system note into a savvy score.

Do you see HR as the accidental ally here, or was this pure procedural poetry? How would you tweak your leave game in a lame-duck gig to snag similar spoils? Drop your debriefs below, we’re all ears for your encore tales!

Jeffrey Stone

Jeffrey Stone

Jeffrey Stone is a valuable freelance writer at DAILY HIGHLIGHT. As a senior entertainment and news writer, Jeffrey brings a wealth of expertise in the field, specifically focusing on the entertainment industry.

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