Oops I did it again…

So I made a mistake last week.

I was building a new newsletter template using our Figma plugin, and during the export process, I accidentally removed an apostrophe from some dynamic content. That tiny apostrophe was the difference between “Hey Sarah” and “Hey {$name|default(’email friend’)}” showing up in everyone’s inbox.

The email went out to around 700 people before it could be stopped—only a small portion of our list, but still not exactly the personalized experience I was going for.

But here’s the thing—I didn’t send a follow-up “oops” email. It was a minor mistake that didn’t really warrant drawing more attention to it. Some people probably noticed, but most probably didn’t.

And that got me thinking about Oops emails. So I did some digging through our Email Love collection and discovered something interesting: oops emails are way more common than you’d think. We receive them every month from brands making all sorts of mistakes.

When should you send them? When shouldn’t you? And how do you turn an embarrassing mistake into something that actually drives engagement?

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Some Oops emails we recently received

We collect oops emails on Email Love pretty regularly (mistakes are more common than you’d think), and I’ve noticed some patterns among the brands that handle them really well.

Art Finds: Own It and Honor It

Art Finds sent out an email promoting a “50% off over $750” discount that should have read “$7.95.” That’s not a typo—that’s a pricing disaster.

But instead of trying to backtrack, they leaned into it with humor: “Can we blame Friday afternoon-itis?” Then they did something brilliant—they honored the original offer. Sure, it probably cost them money upfront, but the goodwill (and the stories people told about their integrity) likely paid for itself.

Plus, they didn’t waste the email. Below the oops message, they included actual artwork people could buy. Smart move—if you’re already in someone’s inbox apologizing, might as well remind them why they signed up in the first place.

47 Brand: The Stealth Oops

47 Brand’s approach was different. Their welcome email automation had apparently broken for a few days, missing new subscribers. Instead of a formal apology, they just updated the subject line: “Oops, you never received this. Here’s 50% off your first purchase.”

The email itself looked like a normal welcome offer. Clean, simple, effective. The “oops” was only in the subject line, turning a technical failure into a compelling reason to open.

Francesca’s: Website Drama

When Francesca’s website crashed during a summer sale (because their traffic was higher than expected), they followed up with: “Well, that was awkward. Our site had a little tech drama yesterday, but she’s back and serving the cutest fits.”

I love the personification of their website and the casual tone. It acknowledges the problem without dwelling on it, then immediately redirects to the solution.

Speechify: The Upgrade

Sometimes your “mistake” is actually good news. Speechify sent an oops email saying they’d mentioned a 40% discount in their previous email, but subscribers actually got 50%.

This is brilliant psychology—instead of feeling like they made an error, subscribers feel like they’re getting an unexpected bonus.

Dia & Co: The Forward Approach

This one’s my favorite. Deer & Co sent what looked like a plain text email—but it was actually designed to look like their founder was forwarding the original HTML email with a personal apology note above it.

The visual trick made it feel incredibly personal and authentic, like getting a direct message from the CEO rather than another marketing email.

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When to Send an Oops Email (And When Not To)

Not every mistake deserves an email. Here’s my framework:

Send an oops email when:

• The mistake affects the customer experience (broken links, wrong pricing, incorrect product info)
• The error could cause confusion (wrong event dates, incorrect instructions)
• There’s a legal or compliance issue (missing unsubscribe links, incorrect terms)
• You can turn it into an opportunity (like Speechify’s “accidental” upgrade)

Don’t send an oops email when:

• The mistake is minor and most people won’t notice (like my personalization fail)
• Pointing it out would create more confusion than clarity
• The error doesn’t impact the subscriber’s ability to take action
• You’re just being a perfectionist (trust me, we’ve all been there)

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Oops Email Best Practices

If you do need to send that follow-up, here’s how to make it work:

Lead with personality, not panic

Skip the corporate “We sincerely apologize for any inconvenience.” Instead, acknowledge the mistake with your brand voice. A little humor goes a long way, but read the room—a pricing error might warrant a more serious tone than a broken image.

Make it right

If your mistake cost people time, money, or confusion, fix it. Honor incorrect pricing, extend deadlines, or provide clear next steps. Your reputation is worth more than the short-term cost.

Don’t just apologize—add value

Since you’re already back in their inbox, give them a reason to stay engaged. Include helpful content, showcase products, or offer something extra as an apology gesture.

Keep it simple

Oops emails shouldn’t require a PhD to understand. Clear subject line, brief explanation, obvious next steps. Done.

Time it right

Send your correction quickly, but not so fast that you make another mistake. If you’re using send time optimization like we do, contact your ESP to stop the campaign before it reaches everyone.

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The Silver Lining

Here’s the counterintuitive truth about oops emails: they often perform better than regular campaigns. Why? Because they feel human. They show there are real people behind your brand, people who make mistakes just like your customers do.

The brands that handle mistakes well don’t just recover—they build stronger relationships. Customers remember companies that own their errors and make things right.

So the next time you spot a typo after hitting send, take a breath. Ask yourself if it really needs a follow-up. And if it does, remember that sometimes the best marketing emails are the ones you never planned to send.

Have you sent an oops email recently? Or received one that made you actually like the brand more? Feel free to forward it to [email protected] and I will add it to our collection.

Want to see more oops emails? We have a whole gallery of mistake emails and how brands handle them over on our Oops email gallery. Because let’s face it, we’re all human, and humans make mistakes—it’s how we handle them that matters.