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Every email marketer has a story about a send that went wrong. So, we asked around and found some good (or terrifying) ones to share.

When you work in email, sending a mistake is a matter of when, not if. Ask anyone who’s worked in email for a while, and I guarantee they’ll have a story to tell you about an email send that went wrong. Some, like a small typo, are innocent enough. But others, like sending to the wrong list, are a completely different story.

Luckily, email technology has come a long way, and there are helpful resources and features that take the nerves out of pressing send. But this wasn’t always the case, and seasoned marketers have the scars to prove it.

We asked around to gather some of the best email marketing horror stories out there, and here’s what we got.

One letter makes a major difference

As the author of this post (I’m Will, by the way 👋 ) it’s only fair that I kick things off with my own email blunder.

Now, as far as email mistakes go, a typo isn’t too bad. But this one, in particular, was pretty sh*tty.

Once upon a time, I worked at a custom t-shirt printing company, where I managed the weekly newsletter. With how many times I typed “t-shirt” on any given day, you can imagine how easy it’d be to leave out the r in shirt, leaving you with a naughty typo.

While I’d love to say I caught all those typos, I left one in an email, and 200k+ subscribers got to read as I talked about t-sh*ts.

This feels like a good time to plug Grammarly for all your spell-checking needs.

Cut-off catastrophe

Lizzie Newbern, our own in-house Email Marketing Manager, has more than five years of email experience. But not even that much time in email makes you immune to mistakes. Lizzie’s horror story involves a truncated subject line and some really bad luck.

In a previous role, Lizzie was the Email Marketing Manager for one of the top senior living companies in the business. Occasionally they’d host events for the local communities where they’d send an email invite to residents and other interested leads in the area. This event in particular was for a conversation-starting cocktail night, where potential residents could come tour the community and meet some of the residents while enjoying craft cocktails. 

The subject line for the email was “Celebrate the long weekend with cocktails and conversation.” Pretty harmless, right? 

The email was tested, proofed, and sent on its way. But throughout the day, Lizzie noticed the email was getting a lot of responses.

Starting to sweat, she checked and saw replies like “SO inappropriate.” “Wow, so unprofessional.” “Looks like someone didn’t check their subject line cut-off!”

Finally, she found a response that included a screenshot of the subject line as it displayed in their inbox. There, in all its glory, was “Celebrate the long weekend with c***…”

Luckily, the email went out to less than 100 subscribers, so the damage wasn’t too bad. Moral of the story: send a test email and make sure you check the subject line across all device types.

Dark mode faux pas

Justin is an email marketer and Campaign Monitor alum with over six years of email experience. But the thing about email marketing is, technology is always changing. And no matter your experience level, there’s always something new to keep an eye out for.

While Justin builds tests for every email he sends, he once forgot to test a campaign for dark mode compatibility. After the email was sent, he realized parts of his email were completely unreadable in Gmail’s dark mode.

Lesson learned: test, test, test. With tons of different apps and thousands of screen sizes out there, you can never be too careful.

Also, relevant to this point: don’t miss our Guide to Dark Mode in Email.

One email sent, three angry companies

Tiffani Davidson handles lifecycle marketing at Thimble. She’s also the co-admin for Email Geeks. So, needless to say, her email marketing credentials are well established. And with loads of experience, she has some good stories to tell.

Back when she was working on the email team at Academy Sports + Outdoors, she managed to anger three massive companies, all with one email send.

We’ll leave brand names out of this one, but Tiffani was sending out an email promoting a sale for Academy Sports and Athletic Company A. But, she accidentally put the name of their competitor, Athletic Company B, in the subject line instead.

That leaves Academy Sports, Athletic Company A, and Athletic Company B all equally angry.


A testing blunder

Grace is an email marketer turned copywriter. Why? Well, in her words, “I couldn’t afford the therapy I’d need to manage the stress.” 

One time, she was working with a junior designer to create a new email template, and she asked the designer to send her a test. But, she didn’t think to double-check and make sure that the designer understood how to send a test email.

So, instead of receiving a test of the template, the designer accidentally sent out a broken email to their entire list. Of 800k people. *Insert crying emoji*

This feels like a good time to mention our support doc on how to test your emails. You’re welcome.

Wrap up

Email marketing is not for the faint of heart, people. Even the most seasoned email marketers still get send anxiety, send-button shakiness, or whatever you want to call it. But, at least you know you’re not alone.

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This blog provides general information and discussion about email marketing and related subjects. The content provided in this blog ("Content”), should not be construed as and is not intended to constitute financial, legal or tax advice. You should seek the advice of professionals prior to acting upon any information contained in the Content. All Content is provided strictly “as is” and we make no warranty or representation of any kind regarding the Content.
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