Issue #248 All About Email

Hi, {{first_name|friend}}. 👋

Welcome to Issue #248 of All About Email!

Last week was my second guest author of the summer, as we took a look at “Why Being In The Right Room Changes Everything You Know About Email.”

This week, I have my third guest author of the summer and arguably the founder of my summer series (thank you, Vicky) as we explore the “accidental oops” email.

Let’s go! 👇

Some people curate musical playlists for background vibes when working. Others tune into those special mHz "focus frequencies." Me? Most days, I'm deep in repeats of Ricky Gervais, Stephen Merchant, and Karl Pilkington's early-2000s radio show on the XFM vault.

After enough hours listening to those shows, Ricky's business skills become as obvious as his comedic ones.

Long before social media became the default marketing channel, he'd regularly tell listeners to visit his website, join his mailing list, and sign up for updates.

🎉 So when Ricky launched Dutch Barn Vodka and started actively growing an email list, I was delighted. Actually, delighted might be understating it.

I've spent the last eight months talking about how much Ricky Gervais talks about his email list. Ask anyone who's been on a client call with me recently, and they've probably heard me mention it 😅.

I even wrote a blog on it.

So you can imagine my disappointment when an "oops" email from Dutch Barn Vodka landed in my inbox in June.

Not because they sent an oops email. That part I get. Every marketer has been there in some form or another.

😔 No, I was disappointed because this wasn't a genuine oops email.

The message explained that a product launch email had been accidentally sent and that some subscribers may have briefly seen something they weren't supposed to see.

The good news was that they had managed to pull it back. The bad news was that a small group may have caught a glimpse of it before it was recalled.

🚨 Dutch Barn uses Klaviyo as their ESP. And once an email has been delivered from Klaviyo, it can't be pulled back out of someone's inbox.

You can stop a send mid-flight. You can halt what's still queued. But you can't reach into thousands of inboxes and retrieve something that's already landed.

(I triple checked my inboxes for the email they said they'd accidentally sent. It wasn't there.)

🤷‍♀️ So in this case, that "oops" almost certainly never existed.

But most subscribers won't think about that. They're not sitting there wondering about email infrastructure or delivery mechanics. They'll read it, smile, and move on.

💡 But that's exactly what makes it interesting, and slightly uncomfortable.

The email's effectiveness relies on people accepting its framing at face value. It borrows credibility from the idea that something accidental and slightly chaotic just happened behind the scenes.

We've seen the "we accidentally sent this to our entire list" email become its own little genre.

Charlotte Tilbury has used variations of it. Steven Bartlett and Diary of a CEO communications have leaned into similar "leaked" or "not meant for you" framing.

They do the rounds on LinkedIn every time one pops up.

🤔 For me, the real question isn't whether fake oops emails “work”:

🚨 Whether they're building the kind of relationship you actually want with your subscribers.

🧠 Curiosity is powerful. It's one of the most reliable tools in email marketing for driving opens. But curiosity doesn't need to be built on pretending something happened when it didn't.

The best emails I've seen over the years don't rely on manufactured accidents.

They lean into things that are already inherently interesting: a real customer question, a genuine behind-the-scenes moment, an actual mistake, a strong opinion, a launch delay that genuinely changed plans.

🎉 In other words, something real. And you can feel that difference as a reader.

Even if you're not consciously analysing it, there's a sense that what you're reading is grounded in something that actually happened versus something constructed to look like it did.

🫠 That's why this one bugged me.

Dutch Barn has already proven it doesn't need this kind of framing to be interesting. The voice is strong. The humour is strong. The audience is already engaged.

💡 So the fake mistake feels less like a clever play and more like an unnecessary one.

I'm a fan of curiosity in email. I'll always be a fan of curiosity in email. I just don't think it ever needs to be smuggled in as an "oops" to do its job.

What are your thoughts, {{first_name|friend}}?

Vicky Smith

What I found most interesting here is that this isn’t really a debate about whether fake “oops” emails generate opens. They probably do.

💡 It’s about what happens when a brand borrows trust to create curiosity.

The technical details about Klaviyo are what initially expose the tactic, but the bigger issue is the relationship being built with the subscriber.

🚨 Most people receiving the email won’t know that a delivered campaign can’t simply be pulled back from their inbox. They’re being asked to accept the story because it sounds plausible.

And that feels particularly unnecessary in this case.

Dutch Barn already has Ricky Gervais, a distinctive voice, plenty of humour and an audience that appears genuinely interested in what the brand is doing. There must be dozens of real stories, opinions, and behind-the-scenes moments they could use to spark curiosity without having to manufacture one.

✅ That’s the lesson I’d take from this:

See you next week, {{first_name|friend}}. 👋

Simon

Every week, as I write this newsletter, I'll share the track of the moment to create an unbelievably eclectic playlist just for your inbox.

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This week's excellent and insightful email news & tips:

If you have any questions about this email or email marketing, please reply, and I will get back to you as soon as possible.

I hope you have a great week! 👋