June 10, 2026 at 9:21 pm

IT Guy Spends Forever Troubleshooting a Customer’s Problem — The Cause Was Embarrassingly Simple

by Liz Wiest

Man and woman answering phone calls at a desk

Source: Pexels/Reddit

Customer Service and Tech Support workers have to spend the entirety of their days answering hyper-specific questions from customers who very often don’t know a computer from a calculator. Their job requires a mix of patience, understanding, and ingenuity that other fields can usually get away without.

How would you react if you discovered your very impatient customer with a wild IT request actually had a very simple solution right in front of them? One guy recently shared a wild story about this with Reddit. Here’s what he said.

When a calendar is not a calendar

Happened this week.

I’m a M365 SysAdmin.

A ticket was escalated to me where the user wanted to modify a calendar’s permissions.

Sounds like a typical IT problem.

Ok. Not a big deal.

But I could not locate the calendar.

So doing what any good IT professional would do, I asked for a call over Teams and then requested the user share their screen.

Pretty standard procedure in this day and age.

Once connected and seeing what they see, I made the request.

“Please show me how you access this calendar.”I’m expecting Outlook > Calendar > specific calendar. But nope!

The user opened File Explorer, navigated to the File Server, and through several folders.

Sounds like they’re not the most tech-savvy.

The last folder led to a file called 2026 Calendar.

And it’s an Excel file! No wonder I couldn’t locate the calendar anywhere in Exchange!

After that I suggested that maybe we should consider a real calendar for future use. 🤦‍♂️

Whatever this guy is getting paid, it’s definitely not enough.

If you enjoyed this story, check out this post about an IT department who keeps receiving tickets for a company that was previously spun off.

Let’s see what the Reddit community had to say about this one.

The comments section immediately empathized with IT support.
Screenshot 2026 05 26 at 5.57.53 PM IT Guy Spends Forever Troubleshooting a Customers Problem — The Cause Was Embarrassingly Simple

And many with experience chimed in.
Screenshot 2026 05 26 at 6.03.28 PM IT Guy Spends Forever Troubleshooting a Customers Problem — The Cause Was Embarrassingly Simple

Most could relate all too well.
Screenshot 2026 05 26 at 6.03.38 PM IT Guy Spends Forever Troubleshooting a Customers Problem — The Cause Was Embarrassingly Simple

Some jumped at the chance to share stories on their own.
Screenshot 2026 05 26 at 6.04.12 PM IT Guy Spends Forever Troubleshooting a Customers Problem — The Cause Was Embarrassingly Simple

But one person put the whole thing into perspective.
Screenshot 2026 05 26 at 6.04.20 PM IT Guy Spends Forever Troubleshooting a Customers Problem — The Cause Was Embarrassingly Simple

Working in Tech Support isn’t for the faint of heart.

If you enjoyed this story, check out this post about a cashier who met a customer outside of work, and now they can never go back to their old relationship.