Phishing emails are the bread and butter of online scams. While they’re crafted to trick people into handing over their secrets or cash, let’s be honest - scammers don’t always bring their A-game.
Some attempts are so hilariously bad they’re more like a comedy sketch than a cyber threat. Think typos that would make a grammar teacher cry, demands so outrageous even a soap opera villain would roll their eyes, or the classic “Nigerian prince” who’s apparently still stuck in the 1990s.
Today, we’re pulling back the curtain on the funniest phishing fails ever to grace an inbox. These blunders are good for a laugh, but they also come with a side of education. Because when you know what to look for, spotting scams isn’t just smart - it’s downright entertaining.
What is a phishing email?
A phishing email is like a wolf in sheep’s clothing: a deceptive message designed to steal personal data or money while pretending to be something trustworthy. These emails mimic legitimate organizations, from your bank to your HR department, and rely on urgency, fear, or curiosity to get you to act without thinking.
Here’s the good news: once you know what to watch for, these scams lose their edge. In fact, some of them are so poorly executed that they become comedy gold. Typos, laughable requests, and scammers who don’t understand basic grammar? Priceless. Let’s explore nine phishing fails that remind us scammers are people too - just not people you’d ever hire.
9 Funny Phishing Emails That Don’t Seem Real… But They Are
1. Urgent Wire Transfer Request from the "CEO" (Who’s on Vacation)
You’re sitting at your desk when an email pops up from your CEO, demanding a wire transfer ASAP. The kicker? The CEO just posted vacation photos from a tropical beach on Instagram. This scam preys on employees’ fear of authority and urgency, but the execution often falls flat.
The email might include phrases like, “I need this done NOW, no questions asked,” which is exactly how every CEO communicates… in a bad sitcom. Some scammers go as far as spoofing the CEO’s email, but they fail to match their tone or even spell their name correctly. A CFO named “Jessica Bennett” doesn’t suddenly become “Jessika Bennet” because she’s in a hurry.
To avoid falling for this scam, verify these types of requests directly with the alleged sender via phone or another internal method like the company Slack channel. (If the CEO is truly desperate for help, they’ll answer your call - even from the beach!) You should also forward the message to your IT or security team for immediate investigation and resolve to NEVER approve financial transactions without following internal protocols, no matter how urgent the request seems.
2. The IT Department That Asks for Your Password
“Dear User, your account has been compromised. Please send us your password to fix the issue.”
Sure, because IT departments are sitting around waiting for you to hand over your credentials, right?
This scam works because people trust their IT teams, and scammers often add a sense of urgency by threatening account deactivation. But here’s what you need to remember: IT already has the tools to access your account if necessary. They don’t need your password, and they certainly won’t email you at 2:00 a.m. with sketchy instructions to “click here and save your account.”
If you’re ever unsure, hover over the email links. Chances are that they’ll lead you to a domain that looks nothing like your company’s website. And if IT really wanted your password, they’d probably just visit your office and ask for it - not send a poorly written email.
3. "Accounting Needs Gift Cards ASAP!"
Gift card scams are a classic in the phishing playbook. Scammers pretend to be someone in accounting (or even a company executive) asking employees to urgently purchase gift cards for “client appreciation” or “employee rewards.” They’ll ask for the codes to be emailed back, claiming it’s a time-sensitive request.
The hilarity here lies in the sheer absurdity. Imagine your boss asking for $500 in gift cards for an “important client meeting,” but instead of planning the meeting, they’re using Gmail and typing everything in Comic Sans. The excuses for why this can’t wait are often as outlandish as the request.
Remember: no reputable company conducts business with iTunes gift cards. If you’re ever in doubt, pick up the phone and ask your boss directly. Their reaction to the question alone will be priceless.
4. The Vendor Invoice That Misses the Mark
Scammers often impersonate vendors by sending fake invoices to companies and hoping someone pays without question. They get creative with branding, logos, and professional language to make these emails look convincing.
But sometimes, the details don’t add up. The “vendor” might be “XYZ Supplies,” but the email comes from “xyZ_suplies@hotmail.com.” The invoice might include charges for services your company has never used, like “Advanced Widget Optimization” - whatever that means.
The funniest part is that these scammers expect you to pay large sums of money with zero hesitation. As if businesses don’t have finance teams that scrutinize every dollar spent. Before paying any invoice, confirm it with the vendor directly. And if something seems off, trust your gut - it’s probably a scam.
5. The "HR Benefits Portal Update" with a Suspicious Link
“Act now to update your benefits, or risk losing them!”
These emails prey on employees’ trust in HR and their fear of missing out on key perks. Scammers often time these emails during open enrollment periods to make them seem more believable.
The humor here lies in the execution. The email might start with a vague greeting like “Dear Employee” and include a link to something like “hrbenefitsupdate.biz.” You’d think HR would at least know your name, right?
If you’re ever unsure about an email like this, skip the link. Go directly to your HR portal or contact your HR team. They’re probably too busy planning the next holiday party to send vague, threatening emails.
6. "New COVID-19 Policies: Download Attachment"
Even years after the height of the pandemic, scammers are still using COVID-19 as bait. These emails claim to include updated policies or vaccination requirements, but the attachment is usually malware in disguise.
What’s funny is how out-of-touch these emails can be. “PolicyUpdate2024.exe” doesn’t exactly scream “official document.” And yet, the scammers believe people will click on it without a second thought.
If your company truly had a COVID policy update, you’d hear about it through official channels. When in doubt, ask your HR or management team before downloading anything.
7. The CFO Who Misspells Their Own Name
It’s hard to take a scam seriously when the sender, claiming to be your CFO, can’t spell their own name correctly. “Catherine Johnson” becomes “Kathryn Jonson,” and somehow, you’re expected to believe they urgently need a wire transfer.
These scams thrive on urgency and secrecy. The email will include phrases like “Do not involve anyone else!” or “Complete this transfer immediately!” While this might pressure someone into acting quickly, the spelling errors and odd tone often give away the scam.
8. "Please Update Our Supplier Info" (From a Fake Supplier)
“Download the latest security update from MicroS0ft.” You have to admire the audacity of scammers who think one typo won’t raise suspicion.
These emails claim to come from big tech companies like Microsoft or Adobe, urging recipients to download updates to fix security issues. Of course, the “update” is malware.
If you need to update software, always go through official channels. And if Microsoft can’t spell its own name, you’ve got your answer - it’s a scam.
9. The IT Software Update from "MicroS0ft"
“Download the latest security update from MicroS0ft.”
You have to admire the audacity of scammers who think one typo won’t raise suspicion.
These emails claim to come from big tech companies like Microsoft or Adobe, urging recipients to download updates to fix security issues. Of course, the “update” is malware.
If you need to update software, always go through official channels. And if Microsoft can’t spell its own name, you’ve got your answer - it’s a scam.
Why do phishing scams work?
Phishing scams succeed because they exploit human emotions like fear, trust, and urgency. Even when the emails seem laughably bad, they can catch people off guard. Remember, falling for one doesn’t mean you’re not smart - it just means the scammer caught you at the wrong moment.
How do you protect your business from phishing attempts?
Training employees to recognize phishing emails is critical for keeping your business secure. Simulations and regular reminders help employees spot scams before they become problems.
At Jericho Security, we turn phishing defense into an engaging experience. Our training programs empower teams to recognize scams like pros - and maybe even laugh along the way. Either way, your boss (and, by extension, you) will enjoy greater peace of mind.
Protect your business now and laugh later!
While phishing emails can be laughable in their execution, they’re no joke when it comes to the potential damage they can do. Protecting your business starts with empowering your employees to recognize these scams and respond appropriately.
Imagine a workplace where everyone can spot a phishing attempt and laugh it off rather than panic. That’s where Jericho Security can help. With our innovative, AI-powered cybersecurity training, we prepare your team to handle phishing attempts with confidence.
Don’t let scammers get the last laugh. Arm your team with the knowledge and tools they need to stay secure. Book your demo today and turn phishing defense into a skill everyone can master.