October 18, 2025 at 5:47 pm

Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

by Sarrah Murtaza

Man in checkered shirt working in office

Pexels/Reddit

Imagine being on vacation, but your boss emails you asking you to work.

Would you ignore the email, tell your boss no, or agree to work?

This guy was in this situation.

He was willing to work while he was on vacation, but he insisted on being paid for it as a work day not a vacation day.

Check out the full story.

Getting all my PTO paid out

Despite working in a high stress, high tech sales role, I believe that when you’re on vacation (paid time off) you don’t work and disconnect.

Whenever I was on PTO and my manager would request something from me I would email “Are you asking me to work on my time off?”

The answer was always something like “Yes. I really need this done.”

After I worked I would re-claim the vacation time in our employee portal.

UH OH…

I saved every email.

Last week HR launched a new portal that allows us to see vacation time, sick time, etc.

My vacation balance was about 2 weeks short.

When I alerted HR to it, they said that they took back a chunk of time I had reclaimed because they felt I was abusing the system.

He knew how to win this!

Then I sent them every email from my manager asking me to work, documenting that it truly wasn’t time off.

I also included a link to the state law stating that even a minute worked in the day counted as a full day (I’m salaried).

My PTO balance was quickly returned.

YIKES! That’s crazy!

This is how working smart pays off.

Let’s find out what folks on Reddit think about this one.

This user shares a similar experience from their workplace!

Screenshot 2025 09 19 122407 Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

Exactly! This user knows that vacation means no work!

Screenshot 2025 09 19 122421 Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

This user thinks the system was abusing this guy’s PTO.

Screenshot 2025 09 19 122439 Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

This user thinks more people need to join this guy with his schemes.

Screenshot 2025 09 19 122452 Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

This user would have never thought of using emails as a weapon.

Screenshot 2025 09 19 122557 Boss Kept Emailing Employee While They Were On Vacation, So He Demanded To Be Compensated For The Time He Worked While Away

Having proof was key!

If you liked that story, check out this post about a group of employees who got together and why working from home was a good financial decision.