It’s spooky season, and if there’s anything scarier than mysterious creatures lurking in the dark, it’s sending a holiday campaign and realizing something has gone horribly wrong.
You’ve been there: deadlines breathing down your neck, endless rounds of testing, and then the moment of truth. You hit “send,” expecting sales to roll in. But instead? You’re greeted by the sound of crickets. Or worse, something has completely broken.
In the spirit of the season, we’ve rounded up the most horrifying—and yes, now hilarious—stories from email geeks who’ve survived holiday campaign nightmares. We’re keeping the names and faces of these poor souls anonymous so that they aren’t haunted any more than they already are.
Let’s start with a real-life horror movie.
The Email Marketer Who Almost Got Arrested
Imagine: It’s your first Black Friday working in email marketing. You arrive at the office early to make sure everything runs smoothly. But instead of sending emails, you nearly end up in handcuffs.
“I got to the office super early… didn’t know you needed to deactivate the building alarm. The cops showed up, three cars deep, stormed the office, and almost arrested me. I had to call my boss to vouch for me.”
Lesson learned: Don’t get arrested trying to send a promo.
A Home Invasion, But Worse
Let’s talk about when things get really dark. One marketer had all their campaign creative—gone—just weeks before Black Friday. And it wasn’t because of a system failure or bad planning. It was straight-up stolen.
“Our photographer’s home was broken into, and all her equipment—laptop, hard drive, camera—everything, was stolen. We lost all of our campaign creative. We scrambled to reshoot, but two days before Black Friday, the police recovered her stolen property. We had to laugh or we would’ve cried.”
When your holiday season is literally a crime scene, all you can do is hope for a Hollywood ending. Oh, and it doesn’t hurt to start on your creative early. You never know.
When Deliverability Isn’t on Your Side
Now, back to the classics: the dreaded blocklist—aka the graveyard of email marketing.
“A big brand tech company I worked with got blocklisted on Spamhaus Thursday of Black Friday weekend. 90% of their IPs were fully blocked from sending.”
Imagine hitting send on one of the biggest weekends of the year, and poof—your emails vanish into the ether. We know that email marketing can be challenging, but these incidents are the stuff of nightmares!
Pro tip: phone a little friend called the Inbox Monster Client Services Team and rest assured this doesn’t become a reality for your team, too.
Blame It on the ESP
You’ve done your job, but sometimes the system fails you—or a system fails you—and the results are chilling.
“My ESP was down during Black Friday. They had server issues due to volume. Emails didn’t go out, and the login wasn’t responsive. Hours later, we got back in, but we missed our morning rush.”
Another marketer had a similar horror story:
“Our sub-par ESP crashed on Black Friday. TWICE. It wiped out all the email links during our busiest time of year. The only bright side? I’m not there anymore.”
The Human Factor—Because We’re Only Human, Right?
Of course, no holiday campaign horror story would be complete without the good ol’ human error.
“I was so stressed that I accidentally scheduled an email for the night before the promotion started. Oddly enough, it converted better than expected. But I still had to send out an ‘Oops, we goofed’ email.”
Then, there’s this gem:
“At a nonprofit, we accidentally listed a phone number that forwarded to an adult hotline. You can imagine the chaos.”
These little hiccups are proof that even in our most chaotic moments, there’s always something to laugh (or cringe) about later.
Couldn’t Handle the Traffic!
So, your emails are killer, all the links work, and everything’s on point… but your site crashes because it can’t handle the traffic.
“Last year, our client’s site went down for 6 hours during BFCM, and they lost high 6 figures in sales. They ended up building their own eCommerce platform to prevent it from happening again.”
It’s safe to say that these stories—though they caused minor heart attacks at the time—are now the stuff of email marketing legends. But let’s avoid adding more horror stories to the mix this year.
At Inbox Monster, we’re here to help make your campaigns more predictable and successful—because let’s be honest, none of us want to end up on the dark side of a Black Friday disaster.
P.S. We’ve already got our iPhone 16/iOS 18 previews live within our tool, so you can even make sure your most tech-savvy subscribers see your creative pixel-perfect. Get started here.
