July 1, 2026 at 11:55 am

He’s On Disability With a Pay Gap and Asked to Use His Unlimited PTO to Cover It — His Boss Said No and Now He’s Struggling

by Benjamin Cottrell

stressed man staring at his laptop

Pexels

Unlimited PTO sounds incredible in theory… until you realize the exceptions far outweigh the benefits.

One employee found that out the hard way after going on short term disability and discovering that state coverage only pays 70% of his income.

To cover the pay gap, he asked his boss if he could use some of the company’s unlimited PTO to cover the remaining 30%. It seemed like a perfectly logical request on its head, but the reality wasn’t near as kind.

Keep reading for the full story.

Boss won’t honor Unlimited PTO while on disability

I’m currently out on short-term disability and the state policy only covers 70% of my income. That 30% gap is really hitting me hard.

My company offers unlimited PTO, and I assumed I could use some of it to supplement the missing 30% while I’m out, essentially using PTO to “top off” my pay to 100%.

He soon learned the powers that be weren’t interested in taking his side.

My boss, however, is refusing to allow it.

Since we are such a small team, we don’t have an HR person and he makes the final decision.

He consults the employee handbook in one last-ditch effort to plead his case.

There’s no written policy I’ve found that explicitly says our “unlimited PTO” can’t be used during short-term disability leave in California.

Seems like I am going to have to donate plasma…

This employee sure is in a tough spot.

Trending and Popular

If you enjoyed this story, check out this post about a person who feels so undervalued they refuse to sign another contract.

Reddit is sure to have a lot to say on the matter.

This user takes the employer’s side.

Screenshot 2026 06 23 at 5.22.42 PM Hes On Disability With a Pay Gap and Asked to Use His Unlimited PTO to Cover It — His Boss Said No and Now Hes Struggling

This employee may have somewhat of a fundamental misunderstanding about how PTO operates.

Screenshot 2026 06 23 at 5.23.38 PM Hes On Disability With a Pay Gap and Asked to Use His Unlimited PTO to Cover It — His Boss Said No and Now Hes Struggling

Unlimited PTO is kind of a well-known scam at this point.

Screenshot 2026 06 23 at 5.25.06 PM Hes On Disability With a Pay Gap and Asked to Use His Unlimited PTO to Cover It — His Boss Said No and Now Hes Struggling

This user worries this employee may be unintentionally setting himself up for trouble.

Screenshot 2026 06 23 at 5.26.12 PM Hes On Disability With a Pay Gap and Asked to Use His Unlimited PTO to Cover It — His Boss Said No and Now Hes Struggling

Nobody wants to hear this when they’re injured and struggling, but the employee’s biggest mistake happened long before the disability leave.

It actually happened the day he accepted “unlimited PTO” as a real benefit without asking what it actually covers, who approves it, and what happens when you need it during a medical situation.

That’s not his fault in a moral sense, because companies design these policies to sound comprehensive so nobody asks those questions. But it is the overarching lesson.

Unlimited PTO exists because it saves companies money, not because it actually helps people. Full stop.

[sifter_post_promo heading="Trending and Popular" link="https://twistedsifter.com/2026/06/manager-refuses-to-pay-approved-overtime-so-employee-stops-working-extra-hours-and-lets-clients-complain/?utm_source=IN-ARTICLE&utm_medium=IN-ARTICLE&utm_campaign=IN-ARTICLE" button="Read The Drama"] If you enjoyed this story, check out this post about an employee who stops working extra hours after overtime is denied, leaving clients in the lurch.

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Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.