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I Messed Up (And Here’s What I Learned About ESP Migrations)
If you received a welcome email from me last week that felt… familiar, I’m sorry. That was me. I’m the problem, it’s me.
Yeah, it happens. It doesn’t look great when the guy running an email inspiration site sends duplicate welcome emails, but we’re not saving lives here. Hopefully no one was too offended. I do apologize for the mess up though.
Here’s how it went down.
I finally pulled the trigger on migrating Email Love from MailerLite to Customer.io. I’d been putting it off forever because, honestly, ESP migrations are probably my least favorite part of working in email. (I’ve been doing this for close to 20 years and I still dread them. Is it anybody’s favorite? If so, please reach out because I have questions.)
So there I am. It’s late. I’m tired. But I’m determined to get this thing done in one sitting. I uploaded our data, set up all our templates, recreated our segments. Everything looked good.
Then I noticed I’d tagged some data with the wrong source. Easy fix, right? I redownloaded the data and reuploaded it to Customer.io.
That’s when things went sideways.
The re-upload triggered our “Logged in user” journey, which promptly sent welcome emails to a bunch of people who had already received them. Rookie mistake. A few people unsubscribed. A couple replied asking if they’d received a weird email. What can I do other than laugh?
Now, you might be wondering why I didn’t send an oops email to clean things up. I thought about it. But here’s my take: you only need to send a correction when it’s actually necessary. Like when you sent a sale email with the wrong date, or you need to update subscribers for legal reasons, or they’ll have a genuinely bad experience if you don’t clarify something.
In my case? It was just a duplicate welcome email. Annoying, sure. But sending another email explaining what happened would probably be more annoying than the original mistake. Sometimes the best move is to just move on.
The Silver Linings
Despite the chaos, there were a few wins buried in this mess.
First, Customer.io is going to let us do a lot more with our data and personalization long term. MailerLite served us well, but we needed a platform that could grow with us. The migration was overdue.
Second, because we built all of our templates with the Email Love Figma Plugin, exporting everything from Figma and uploading it into Customer.io took no time at all. No rebuilding templates from scratch. That saved me hours on an already long night. (Shameless plug, but it’s true.)
Third, this whole experience reminded me that mistakes make for good content. Which brings me to the real reason I’m writing this post.
Oops Emails Done Right
I’m not the only one causing a stir in inboxes. We see oops emails come through Email Love all the time, and some of them are genuinely great. Here are five recent favorites that show how to handle mistakes with grace—and sometimes turn them into opportunities.
Ugmonk: The Wrong Link Recovery
Jeff Sheldon accidentally linked to the Ugmonk site instead of the actual NYT Wirecutter article featuring his Analog system. Classic copy-paste mistake.
His fix? A quick, honest correction that actually became more engaging than the original email. He opens with “Oops! In my excitement to share the NYT feature, I accidentally linked the image to our site instead of the article.” No corporate speak. No groveling. Just a human admitting a human mistake.
What makes this one great is that Jeff uses the correction as an opportunity to share more of the story. He includes a quote from the Wirecutter article and talks about how unexpected the feature was. The mistake became a reason to connect more deeply with his subscribers.
This one isn’t technically an oops email, but it’s brilliant reframing.
Echo ran out of their Flask inventory on Amazon during Prime Day—faster than they expected. Instead of just saying “sorry, we’re out of stock,” they sent an email extending the same 20% discount on their own site with free shipping included.
“We Didn’t Expect to Sell Out This Fast!” The subject line turns potential disappointment into excitement. The email itself is clean, the CTAs are crystal clear, and they reinforce trust with their money-back guarantee and easy returns messaging in the footer.
A problem became a second chance to buy. And they probably made better margins selling direct anyway.
Francesca’s: The Playful Tech Drama
“Well that was awkward…” is such a good way to open an apology email.
Francesca’s had site issues and instead of sending a stiff “we experienced technical difficulties” message, they leaned into it. Sparkle emojis around “tech drama.” One sentence acknowledging the problem. Then straight into their 50% off sale.
They don’t over-explain. They don’t grovel. The phone mockup showing the site working again says “we’re back” without belaboring the point. It’s light, it’s on-brand, and it moves on quickly.
Brooks Brothers: The “Our Error Is Your Gain” Play
This is a classic move and Brooks Brothers executes it well. They sent an email with an error in their clearance sale, and instead of just correcting it, they increased the discount to 25% off.
“Our error is your gain” right there in the preheader. Smart. The email is short and to the point: we messed up, here’s a better deal to make up for it, your pre-summer wardrobe refresh continues now. No lengthy apology, just action.
What I appreciate here is that they don’t dwell on what the original error actually was. It doesn’t matter. What matters is that subscribers now have a reason to shop. Turn the mistake into a promotion.
Groove Life: The Caffeinated Bundler
This one made me laugh. Groove Life’s bundle tool broke on a Friday (relatable), and their correction email leans all the way into the humor.
“Our Bundler clocked out early Friday like it had weekend plans.” That’s such a good line. Then: “Don’t miss your second chance. Our Bundler’s been properly caffeinated and won’t flake this time.”
It’s casual, it’s funny, and it’s signed by Corinne from their CX team—not a faceless brand. The personal signature adds warmth. They acknowledge the problem, make you smile, and give you clear CTAs to go bundle your rings. Perfect tone for their audience.
What Makes These Work
Looking at all five, a few patterns stand out.
They’re honest without being over-apologetic. Nobody wants to read three paragraphs of “we’re so sorry, we can’t believe this happened, please forgive us.” Acknowledge it. Keep it brief. Move forward.
They turn the mistake into an opportunity. Ugmonk got to share more of the Wirecutter story. Echo drove traffic to their own site instead of Amazon. Brooks Brothers sweetened the deal. Francesca’s reminded people about their sale. Groove Life made subscribers smile. Every one of these emails created value beyond the apology.
They maintain brand voice. Ugmonk stays personal and founder-driven. Echo stays clean and benefit-focused. Francesca’s stays playful and young. Brooks Brothers stays classic and polished. Groove Life stays casual and fun. A crisis isn’t an excuse to sound like a robot.
They don’t dwell. The ratio of “here’s what went wrong” to “here’s what you can do now” skews heavily toward the latter. Nobody wants to marinate in your mistake with you.
My Takeaways (And Yours)
Don’t rush your ESP migrations. Or if you’re going to do it yourself, at least don’t do it late at night when you’re tired and just want to be done. Better yet, hire an agency or team with a solid process for this stuff.
Test your journeys before going live. Especially the ones that trigger automatically based on data imports. Yes, I should have known this. Yes, I’m a little embarrassed.
Know when an oops email is necessary versus overkill. Sometimes the follow-up causes more friction than the original problem.
And if you do need to send one, take a page from these brands. Be honest, be brief, stay on-brand, and if you can, turn the mistake into something valuable for your subscribers.
At the end of the day, it’s email marketing. We’re not usually saving lives. I’ll chalk this up as a key learning and hopefully have a team handling migrations for me in the future. Ideally we never have to migrate again.
If you got that duplicate welcome email from me? Thanks for sticking around. I promise I’m usually better at this.
Much love,
Andy
Email: [email protected]
Twitter: @emaillove
