Oops! Our Most Embarrassing Tech Stories

We’ve all had it happen: you get a little too comfortable with autocorrect, and all of a sudden you’ve sent a horrifying text to your mother-in-law when all you wanted to do was ask if she wanted to come over for dinner at six. And then there are the times when the real world decides to assert its dominance over our digital fantasy world. How many of us have fished our iPhones out from bodies of water and hopefully dumped them into bags of rice?

Devices that cost us thousands of dollars brought low by the humble toilet. PowerPoint presentations gone wrong, errant sleeves sending coffee cups swan diving onto coworkers’ keyboards, financially illiterate pets making our expensive tech toys their expensive chew toys. Who can forget the lawyer who got his 15 minutes of fame when he couldn’t remove the cat filter over his face in a courtroom Zoom call? There are so many ways our favorite gadgets can humiliate us. Below, some iPhone Life readers have been brave enough to share with us their most embarrassing tech stories.

New iPhone and Apple Watch. Went to a funeral. Turned off iPhone but didn’t know my watch could still ring. Yep, it rang, and of course, everyone turned and glared at me.

- Anonymous

Short but devastating. In this day and age, you really have to worry about being embarrassed by your own watch. I give this story 3 out of 5 calls at inappropriate times.

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To follow this new contender for saddest short story ever written, let’s have Jacklyn’s very long, very bad day.

You should know this all happened within a 12- to 13-hour period. My bathroom is very, very small. I’ve been trying to find possible ways to make it less cluttered and still be able to have my daily essentials in it. You should also know that I’m the type of person who constantly misplaces items or forgets where my key, phone, etc. is.

One morning I was running a little behind and didn’t want to be late for work. I kept running into my bathroom to grab something off the shelf above my toilet. I have a cabinet about two or three feet above my toilet, but I sometimes forget to shut the toilet lid to keep from accidentally dropping anything in it.

While I was rushing, I grabbed for a beauty accessory from that cabinet and accidentally dropped my new iPhone in the toilet. Then as I was trying to dry my phone, I went to reach for some tissues in that same cabinet and forgot that I had my Beats Fit Pro earbuds on top of the tissue box. They fell in the toilet as well.

Unfortunately, it does not end there. After this disastrous morning, I was finally home from work and unloading groceries I just bought. I’m going back and forth, rushing around again because all I wanted to do was put my feet up and have a much-needed glass of wine.

Well, when I was done putting my groceries away, I realized that I couldn’t find my iPad anywhere! I was racking my brain. I even thought I might have left it at work. All of a sudden, something just clicked. I opened up my freezer, and my iPad was in it. Must have been in there at best for 45 minutes.

In closing, I thank God for paying extra for an extended and better warranty!

-Jacklyn C.

Wow, Jacklyn! That is one terrible, horrible, no good, very bad day. At least it wasn’t a very expensive one, too. Let that be a lesson for all of us clumsy folk: get the extended warranty. I give this story 4 out of 5 shattered iPhone screens.

Next up, we have another story you’ll have a hard time forgetting.

I was at a church lectureship with 30,000 other Christians. There was an extremely popular preacher that everyone had gathered to hear. He put his portable mic on before going to the men’s room and put this PowerPoint up on the overhead from his phone. Then his grandson called him on FaceTime. When he answered it, it shut off the PowerPoint and put the FaceTime on the overhead. Everyone in the audience could hear him using the men’s room.

-Linda L.

It’s kind of cheating to use someone else’s embarrassing moment, but I’ll allow it because this is just too funny (and mortifying!). 4 out of 5 text messages from your best friend appearing on the screen while you’re giving a work presentation.

I brought my brand-new iPhone home and plugged it in for the first time on my kitchen counter. My husband witnessed a strange incident. Our darling kitty jumped up on the counter and mistakenly thought the power cord was a mouse tail. She pulled on it, and to his horror, the phone plopped into the sink, which was full of hot water and unwashed dishes. The phone did not survive, but thanks to Apple Care, it was replaced very quickly. Kitty was not punished but got her own play phone with a ”mouse tail.” Wish I had a photo!


Rosemary, let’s not give everyone else’s cats ideas on how to get new toys! 3 out of 5 chewed-up Lightning cables.

Next up is a genre I like to call “iPhone Life After Dark.” These stories are a bit spicy, so I’ve edited them to maintain the air of sophistication and dignity that we, the iPhone Life team, value so highly (but not highly enough to not include these stories at all).

I thought I texted, “I’ll meet you to go over it at six.” My phone took over and said, “I’ll meet you at the corner for…”

-Sue C.

Well, you can use your imagination. Let he whose phone has never sent an accidentally suggestive text cast the first stone. 3 out of 5 monocles shattering upon receipt of a scandalous message.

While speaking to my daughter on the phone, she mentioned [redacted to protect the innocent] had his first girlfriend. My response was, “I expect ya better buy some condoms!”

A little later, while checking my email, I noticed that Alexa had ordered three dozen large condoms! I had no idea at the time who had put in the order and falsely accused my 40-year-old son of using my account! I called Amazon to cancel the order and told them I never placed it. They told me “Alexa” did.

When I said, “I expect ya,” it must have heard “Alexa,” and put in the order. Once canceled and refunded, I thought that was the end of it! Boy, was I surprised and embarrassed a few days later, when I received a notification on my phone while I was waiting for a meeting to begin. I was told that my package containing three dozen condoms had been delivered! I am a seventy-two-year-old widow!! Thanks, Alexa!

Alexa is no longer allowed to listen in on my conversations, and I will never have my notifications announced unless I’m home alone!


I’ve got to say, Anonymous takes the cake here. Not only did she accidentally order three dozen—ahem—adult accessories, but she then falsely accused her son of being responsible and had the delivery of said adult accessories announced in a work meeting! That’s it, folks, pack it up. This is the one. 5 out of 5 reasons to never trust Alexa again.

Thank you again to everyone who shared their embarrassing tech stories with us. Even if your story wasn’t included, rest assured I humiliated myself laughing at it while I forgot my mic was on in a Zoom meeting.

If you are cursing the missed opportunity to make hay from your mortifying tech disaster, make sure to subscribe to our Tip of the Day newsletter. You’ll not only get helpful Apple device tips from us every day, but you won’t miss the next call for your best tech-related stories.

Illustration by Mikaila Maidment, mikailamaidment.com

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Author Details

Elisabeth Garry's picture

Author Details

Elisabeth Garry

Elisabeth Garry is an Associate Editor for iPhone Life. Formerly of Gartner and Software Advice, they have six years of experience writing about technology for everyday users, specializing in iPhones, HomePods, and Apple TV. As a former college writing instructor, they are passionate about effective, accessible communication, which is perhaps why they love helping readers master the strongest communication tools they have available: their iPhones. They have a degree in Russian Literature and Language from Reed College.

When they’re not writing for iPhone Life, they’re reading about maritime disasters, writing fiction, rock climbing, or walking their adorable dog, Moosh.