Holiday phishing scams are getting a boost from AI; messages look more polished, more local, and harder to spot. This guide walks your team through the most common holiday scams, a 60-second gut-check before clicking, and what to do if someone slips up, so your Milwaukee business can head into the season a little safer.
TL;DR:
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Phishing remains one of the most common ways attackers break into businesses—and holidays make it easier for fake messages to blend in.
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AI now helps scammers write clean, convincing emails and texts, so bad spelling isn’t a reliable red flag anymore.
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Employees should watch for fake shipping texts, order confirmations, reward offers, charity appeals, and password reset/MFA prompts.
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Train staff to pause for 60 seconds: verify sender, avoid logging in from links, and double-check domains before they click.
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If someone does click, fast, blame-free reporting to IT or your MSP gives you the best chance to contain damage.
Every holiday season, inboxes and phones fill up with:
- “Your package is delayed, click here”
- “Confirm your order or it will be cancelled”
- “You’ve earned a reward, claim it now”
In 2024, phishing remained one of the top reported cybercrimes, and multiple reports estimate that phishing and related scams kick off a large share of global breaches, often 30% or more.
On top of that, research shows that human error and social-engineering scams account for the majority of breaches, not exotic zero-days.
The twist in 2025: attackers are using AI to write cleaner, more convincing messages. Fewer typos. Better branding. Local details.
Your staff needs an update. Here’s a guide you can put in front of your team before the rush hits.
Why the holidays are prime time for scammers
The holiday season is perfect cover for attackers:
- People are getting more shipping notifications than usual
- Everyone is juggling sales, year-end invoices, and personal shopping
- Staff are out on PTO, and coverage is thinner
- People are in a hurry and more likely to click first, think later
It’s not just “tech people” who are targeted. Anyone who touches money, data, or logins is fair game.
How AI has changed phishing emails and texts
Old training told people to look for:
- Bad spelling
- Weird capitalization
- Broken English
That still helps, but AI can now generate messages that sound polished and local.
What’s changed:
- Emails that look like real Amazon, UPS, FedEx, or USPS emails
- Messages that reference your city or local delivery hubs
- Fake login pages that are nearly identical to the real thing
The red flag to emphasize now is “unexpected and asks you to click or log in”, not just bad grammar.
Five holiday scams your employees will see
You can literally copy and paste this list into an internal PSA or training email.
1) Fake shipping texts
“Your package is delayed / needs new delivery instructions. Click here to update.”
Red flag: Shortened or weird links, urgent language, and requests to log in or pay a fee.
2) Fake order confirmations
“You placed an order for $742. Click to cancel if this wasn’t you.”
Red flag: You don’t recognize the order, the sender address is slightly off, and the “cancel” button goes to a login page.
3) Gift card or “thank-you reward” scams
“You’ve earned a $100 gift card for being a loyal customer.”
Red flag: You never signed up for the program, and they want personal details or card info.
4) Fake charity and donation emails
“Urgent appeal” messages that use real-looking logos and emotional stories.
Red flag: Pressure to donate via sketchy links or crypto, not through trusted platforms.
5) Fake password reset or MFA prompts
“We noticed suspicious activity. Log in now to secure your account.”
Red flag: The link doesn’t match the real domain, or the email comes out of nowhere.
A 60-second gut-check before you click
Train your team to slow down for one minute and run this checklist:
- Do I recognize the sender and the context?
Not just the name, look at the full email address or phone number. - Can I get to this information another way?
Instead of clicking, open your browser and go directly to Amazon, UPS, your bank, etc. - Is it asking me to log in or pay from a link?
That’s a classic phishing move. Go to the website yourself instead of using the link. - Does the link look right?
Hover over links on a computer. If the domain is off by even one letter, bail. - Does it feel rushed or threatening?
“Act now or lose access” is a sign to slow down, not speed up.
What to do if someone clicks
No shame, no blame. The longer people wait, the worse it gets. Make sure your staff knows:
- Tell IT or your MSP immediately. Earlier is always better.
- If you entered a password, change it right away (and anywhere else you reused it).
- If malware was downloaded, stop using the device and get it checked.
- If money moved, call the bank or payment provider as quickly as possible.
The message should be: “If you think you messed up, we want to know fast, not perfect.”
How Stamm Tech helps Milwaukee teams stay ahead
For local SMBs, we typically help with:
- User-friendly training that uses real-world examples, not fear and jargon
- Phishing simulations to measure risk and track improvement
- Email and web filtering tuned for current scam patterns
- Incident response playbooks so everyone knows what to do if something slips through
You don’t need your staff to be security experts. You just need them to pause, check a couple things, and know who to call.
If you’d like a one-page PDF version of this guide to send to your team, we can help you put that together.
FAQ
Q1: What is phishing?
Phishing is when attackers send emails, texts, or messages that pretend to be from trusted companies or people to trick you into clicking, logging in, or sharing sensitive information.
Q2: Why do phishing attacks spike around the holidays?
Because people are busier, getting more shopping and shipping messages than usual, and are more likely to click quickly without double-checking. That makes it easier for fake messages to blend in.
Q3: How has AI changed phishing emails and texts?
AI tools help attackers write more polished, convincing messages with fewer typos and more realistic branding. That means employees can’t rely on bad grammar as their main red flag anymore.
Q4: How can I tell if a shipping text is fake?
Be suspicious if the link looks strange or shortened, if it asks you to pay a fee to receive a package, or if it references an order you don’t remember. When in doubt, ignore the link and check your orders directly in the retailer’s app or website.
Q5: Will our spam filter catch all holiday phishing attempts?
No filter is perfect. Many phishing emails and texts still get through, especially targeted ones. That’s why user awareness and simple checks are so important.
Q6: What should employees do if they clicked on a suspicious link?
They should contact IT or your MSP immediately, change any passwords they entered, and stop using the device if it may be infected. Fast reporting gives you a much better chance to contain the problem.
Q7: How can Stamm Tech help our team stay safe?
Stamm Tech can provide training in plain English, run phishing simulations, tune your email and web filtering, and build a simple incident response plan so your team knows exactly what to do when something looks off.