Holiday Hack Season: Why Cybercriminals Target Small Businesses in November and December

A Seasonal Spike in Cybercrime

Every year, the weeks between Thanksgiving and New Year’s see a sharp rise in data breaches, phishing scams, and ransomware attacks. Employees are working remotely, teams are short-staffed, and inboxes overflow with holiday deals, invoices, and shipping updates. That combination makes it easy for a single careless click to cause major damage.

According to recent FBI data, reported phishing incidents increase by nearly 40% during the final quarter of the year. Small businesses and nonprofits are especially at risk — not because they’re careless, but because they’re busy and stretched thin.

“Hackers know that during the holidays, everyone’s guard is down,” notes one cybersecurity specialist. “They target small organizations that don’t have 24/7 monitoring or formal IT teams. It’s low effort, high reward.”

Why the Holidays Are Prime Time for Cybercrime

1. Distraction and staffing shortages
   With vacations, seasonal employees, and remote work, fewer eyes are watching for suspicious messages or login alerts.

2. Increased digital transactions
   Businesses are sending year-end payments, nonprofits are collecting online donations, and vendors are pushing invoices — all prime opportunities for email spoofing and fraudulent redirects.

3. End-of-year urgency
   Phrases like “Please send payment before December 31” or “Confirm before offices close” create false urgency that makes employees skip verification steps.

4. Seasonal scams
   Fake charity drives, phishing emails disguised as shipping notifications, and holiday e-cards carrying malicious attachments are all common during this period.

A Real-Life Lesson Close to Home

A small Chicagoland manufacturer received what looked like a legitimate request from a long-time supplier: an email asking for updated banking details before year-end. The accounts payable clerk, under pressure to close the books, processed the change without a second thought.

By the time the next payment went out, $48,000 had disappeared into an overseas account. Their cyber insurance policy covered most of the loss, but the business still endured weeks of downtime, investigations, and IT restoration.

The lesson? Even experienced staff can be tricked when timing and familiarity collide.

The Four Most Common Holiday Scams

Scam Type What It Looks Like Result

Phishing Emails “Your UPS delivery failed — click to reschedule.” Stolen credentials, malware infections

Business Email Compromise (BEC) “Can you wire this payment before we close for the holidays?” Direct financial theft

Fake Invoices or Charities Invoices for “holiday donations” or fake vendors Data exposure, payment loss

Malicious Attachments “Animated greeting cards” or “holiday party invites” Ransomware or spyware installation

How to Protect Your Business or Nonprofit This Season

1. Refresh employee training before Thanksgiving.
A simple 10-minute refresher can prevent major losses. Remind employees to verify unexpected requests, hover over links before clicking, and never send gift cards or payments without verbal confirmation.

2. Enforce multifactor authentication (MFA).
MFA remains one of the easiest and most effective defenses against stolen passwords. Require it for email, accounting, and cloud logins.

3. Review vendor and donation platforms.
Double-check that payment portals use encryption (look for “https”) and that banking details haven’t been altered.

4. Strengthen backup and recovery plans.
Maintain both cloud and offline backups in case ransomware locks you out of your systems.

5. Review your cyber coverage.
Confirm that your policy covers ransomware, social engineering fraud, and business interruption. If your operations or software changed in 2025, your exposure has changed too.

What Cyber Liability Insurance Covers

Even the best prevention can’t guarantee protection. A comprehensive cyber liability policy can help your organization recover quickly and affordably by covering:

• Forensic investigation and data restoration costs

• Ransomware payments and negotiations

• Third-party liability if customer or donor data is compromised

• Legal and regulatory response

• Public relations and credit monitoring services

• Lost income during downtime or system restoration

For many small organizations, the cost of a cyber policy is comparable to a few dollars a day — and it can be the difference between surviving an incident or shutting down entirely.

Illinois Businesses Face Growing Risk

In Illinois, both businesses and nonprofits are subject to strict data privacy and breach notification laws. Any organization collecting personal, donor, or payment information must have safeguards in place — and must notify affected individuals promptly in the event of a breach.

That’s why cyber insurance isn’t just smart; it’s part of responsible risk management. The peace of mind it provides extends far beyond the holidays.

Final Word

The holidays are meant for celebration, not crisis response. A single click on the wrong “holiday greeting” could lock your systems, halt operations, or drain your bank account.

Before year-end, take time to strengthen your defenses, train your staff, and review your coverage.

Contact us today to schedule a Cyber Coverage Review and ensure your organization is protected before cybercriminals make you their next holiday target.

The holidays are supposed to bring joy, not chaos. But for cybercriminals, November and December are prime hunting months — a perfect storm of distracted employees, increased online payments, and reduced IT oversight. While shoppers are busy checking out online sales, hackers are checking out your business’s vulnerabilities.