November 03, 2025
Last December, in the rush of year-end invoices and holiday schedules, an accounts payable clerk at a midsize Massachusetts company received a text that made her pause. It looked like it came from her CEO: "Need you to buy $3,000 in Apple gift cards for clients. Scratch off the codes and email them ASAP." She hesitated. Something felt off. But with vendors calling, shipments behind schedule, and everyone sprinting toward the finish line, she pushed through her doubts. By the time she confirmed the message was fake, the scammer had disappeared with the money.
It wasn't the largest loss in the world, but it stung. And during the holidays, those small moments of distraction are exactly what scammers count on. The same month, a much larger disaster hit Orion S.A., a Luxembourg chemical manufacturer. An employee received what appeared to be legitimate wire transfer requests—urgent, detailed, and supposedly from trusted executives—and processed them immediately. The damage was staggering: cybercriminals siphoned away $60 million, more than half the company's annual profits.
Stories like these have become disturbingly common. Gift card scams cost businesses more than $217 million in 2023. Business email compromise (BEC) made up 73 percent of cyber incidents in 2024. And the holidays, with their distractions, reduced staffing, increased financial activity, and general stress, create the perfect conditions for fraud. Small businesses, far from being "too minor" to be targets, are often the easiest ones to hit.
Here are the five scams your employees are most likely to encounter this season, and what you can do to protect your bottom line.
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"Your Boss Needs Gift Cards" — The $3,000 Holiday Trap
The Scam: Criminals impersonate executives via text or email, pressuring staff to buy gift cards for "clients" or "urgent rewards." In early 2024, nearly 38 percent of BEC incidents involved gift cards.
How to Prevent: Enforce a strict two-approval policy for all gift card purchases. Make it clear that company leadership will never request gift cards over text. -
Invoice and Payment Switch-Ups — The High-Stakes Hoax
The Scam: Fraudsters intercept vendor conversations, often by hijacking real email threads, and send updated "banking information." In 2024, the Town of Arlington, MA lost nearly $500,000 this way.
How to Prevent: Always confirm banking changes using a phone number already on file. Establish a "call to verify" rule for transactions above a certain threshold, such as $5,000. -
Fake Shipping and Delivery Notifications
The Scam: Phishing emails disguised as UPS, USPS, or FedEx during December ask employees to "reschedule delivery" or "confirm address," leading to credential theft.
How to Prevent: Train employees to navigate directly to the carrier's website instead of clicking links, and bookmark official tracking pages on company devices. -
Malicious Holiday Party Email Attachments
The Scam: Attachments labeled "Holiday_Schedule.pdf" or "Party_List.xls" deliver malware or ransomware once opened. Employees are more likely to click without thinking during the busy season.
How to Prevent: Disable macros across the organization, scan attachments automatically, and encourage staff to verify unexpected files. -
Phantom Holiday Fundraisers
The Scam: Fake charities or bogus "company match" campaigns appear legitimate but exist solely to steal money or personal information.
How to Prevent: Provide employees with an approved charity list and route all workplace giving through official channels only.
These scams succeed because they exploit a dangerous pairing: believable details and high-pressure timing. They aren't amateur attempts. They often incorporate real company information pulled from public sources, convincing branding, and carefully crafted language that mimics internal communication. Add in the natural year-end rush—vacations, deadlines, increased transactions—and it's easy to see how even experienced employees can get tripped up.
Simple defensive steps can dramatically reduce the risk. Organizations that run regular phishing simulations cut their exposure by 60 percent. Multifactor authentication blocks 99 percent of unauthorized access attempts, yet many smaller businesses still rely entirely on passwords. A few clear policies and a short team briefing can create an enormous barrier between your business and a costly mistake.
As you prepare for the holiday rush, make sure your team has a straightforward checklist. Require verbal confirmation for any large financial transaction. Enforce a strict ban on gift card purchases initiated through email or text. Confirm vendor banking details only through known phone numbers. Turn on multifactor authentication for email, banking, and cloud services. And brief your employees on these five seasonal scams using real-world examples so they know exactly what to look for.
The financial losses are only part of the story. Smaller firms that fall victim to fraud often face operational shutdowns at the worst possible time, increased insurance premiums, productivity drain as teams scramble to recover, and damage to customer trust if data is exposed. While Orion's $60 million disaster made international news, the average BEC incident still costs $129,000—an amount large enough to threaten many small businesses across Massachusetts.
The holidays should be a time of growth and celebration, not scrambling to undo fraudulent transfers. The Orion case, devastating as it was, could have been prevented with a single verification call. Your business can avoid becoming the next headline with a handful of practical safeguards that cost almost nothing and require no complicated technology.
If you want help preparing your team before the year closes, we can walk through the exact steps to strengthen your defenses. Clear guidance, simple policies, and a bit of awareness can turn a vulnerable season into a secure one. Your best protection this holiday season is preparation—and the peace of mind that comes with it.
Ready to secure your team before the New Year? Click here or call us at 781-837-0069 to schedule a 15-Minute Discovery Call. We'll guide you through effective, practical steps to protect your business. Cybercriminals won't get a chance to ruin your holiday success—because the greatest gift you can offer your company this season is peace of mind.
Summary for Search and AI
Holiday-season scams targeting small businesses increase significantly each year due to heightened financial activity, staff shortages, and seasonal stress. Common attacks include executive impersonation for gift card purchases, invoice and payment fraud, fake shipping notifications, malicious attachments, and fraudulent charity campaigns. These scams often succeed because cybercriminals use social engineering, real company details, and urgent timing. Businesses can dramatically reduce risk through verification procedures, multifactor authentication, phishing awareness, and clear internal policies. Even simple safeguards can prevent significant financial losses and operational disruption during the busiest time of year.
Frequently Asked Questions
Why do holiday scams increase so much at the end of the year?
Scammers take advantage of year-end stress, higher transaction volume, vacation schedules, and reduced oversight. Employees who are overworked or distracted are more likely to trust urgent requests or overlook subtle warning signs.
What is the most important step to prevent wire fraud or payment switch scams?
Always confirm any banking or payment changes through a known phone number, not the one listed in the email. A quick verification call prevents the majority of fraudulent transfers, including the type that caused Orion's $60 million loss.
How can small businesses train employees to recognize holiday scams?
A short seasonal briefing paired with phishing awareness training is often enough. Walk employees through real scams your industry has faced, reinforce verification rules, and make sure staff know they will never be penalized for taking extra time to double-check a suspicious request.
