Funny tales from the frontlines of customer support

Anyone who’s worked in frontline customer support knows what a grueling job it can be. Between angry customers, technical glitches, and the occasional bizarre situation, it’s a role that demands patience, quick thinking, and a good sense of humor. To lighten the mood, we asked folks to share their stories from the trenches — moments where the unexpected, the hilarious, and the downright strange made a lasting impression. Their stories have been edited for clarity.

Apology class is in session

"We had a customer who lost important data — and therefore money — due to a bug. We apologized, refunded their month's plan, and assured them that we'd identified the root cause so it wouldn't happen again. These were the standard steps at the company I worked for.

In response, the customer sent me an article she had written on the 10 steps to a good apology. I could've been offended, but honestly, it was so funny. It was a refreshing break from the monotony, and her article was genuinely good."

Polly wanna crack the case

"Way back in the 1900s, we had to use dial-up modems to connect to the internet via the old wireline copper telephone system. A common selling point of a new PC back then was the speed at which its modem could connect, with 56K being the gold standard.

During this era, I was working the tech support desk for a now-defunct consumer PC company. As a second-tier agent, I handled more complex cases that tier 1 couldn't easily solve. One day, I got a ticket for a modem that wasn’t behaving as expected, so I called the customer.

He said his modem was randomly dialing in the middle of the night, even when the computer was powered off. He’d wake up to the unmistakable sound of the modem initiating a connection. Anyone who's heard it knows that sound well.

Over the course of three days, we tried everything to resolve the issue. When it happened again on the fourth night, we offered to replace the desktop under warranty. The customer accepted, we shipped the replacement, and I followed up with a call to help with setup. Case closed — or so I thought.

The following week, I had a voicemail from the customer. The new machine had repeated the same behavior, but with a twist. After our setup call, he disconnected the PC, moved it to his home office, and left it there — unplugged. That night, he heard the modem dialing again. This time, though, the PC wasn’t even connected to power.

That’s when the customer decided to investigate further.

It turns out, the customer owned a parrot that had learned to mimic the sounds of a dial-up modem. What we had all assumed was a technical malfunction was just a clever bird doing what clever birds do.

It’s a tale from a different era. I realize that now, typing this out — over 25 years ago, but the details still stick with me."

A picture is worth a thousand oopses

"Once, I asked a customer to send me a photo of their order because they reported something wrong with it, and getting photos was part of our procedure. The customer accidentally sent me a graphic photo of themselves tied to the bed. We were on the phone when they sent it, and they were absolutely mortified by the mistake.

I just said, 'Oops! I think you sent me the wrong photo, sir.'

Unflappability is an important skill in customer service."

Sexy T. Rexy

"I was working for EA not long after the Spore launch. If you remember, Spore was a video game where you could create aliens of any shape and size. They just had to be able to walk with legs and have some sort of sensory organs. I received a call from a gentleman with a slight accent, who was calling about an issue where he couldn’t log in to Spore. I pulled up his account and saw in big red letters: 'User has been suspended.'

'Sir, it looks like your account was suspended.'

'What, that's bullshit!' he said.

'Let me take a look at the reason why.'

'Oh, no, that's okay,' he quickly replied.

But before I could stop, I’d already clicked on the suspension notice.

The user was suspended for a TOS violation: Inappropriate creature. Creature name: Penissaurus Rex. It was, indeed, a penis with two legs. The user had described it as 'The big and mighty penisaur' and added some other lewd details that I can’t quite remember.

'Uh, sir, it says you were banned for a pen—'

'That will be all, thank you.'

Click

Easiest notes of my life."

BBQ gone wrong

"This isn’t my story, but it’s one a colleague dealt with involving a customer who was well-known to us at the time. The customer absolutely loved The Sims but sometimes struggled with distinguishing between the game and reality, which understandably could be emotionally challenging.

One day, my colleague answered the phone, but before he could get out his standard intro, he heard:

'MY FAMILY IS DEAD!!' followed by a fair bit of sobbing.

'Hey, Miss Tiffany,' he said. [Name changed to protect the customer.]

'THERE WAS A FIRE!' she cried.

'It's gonna be okay. We can fix it,' he assured her.

'THERE WAS A BARBECUE AND AND—'

'Okay, is The Sims open right now?' he asked.

Sniffling, she replied, 'Yes.'

'Okay, we're gonna hit escape, and in the menu that pops up, do you see the option that says "Load"?'

'Yes.'

'Okay, we're gonna click on that and...'

Suffice it to say, everyone came out of that one okay."

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