The Executive’s Guide to Holiday Cyber Safety

Every year, as businesses gear up for their busiest season—from Black Friday through New Year’s—cybercriminals amplify their efforts. These periods bring increased transaction volumes, reduced staffing, and heightened human error, making enterprises prime targets for a variety of attacks. Here’s a look at recent trends and real-world examples that highlight the urgency for cybersecurity leaders to stay vigilant during this critical time.

Why Holiday Seasons Are a Hotbed for Attacks

• Skeleton crews on duty: Security teams are often reduced by 40–60% over holidays, which can delay detection and response—IBM found that threat detection times can nearly triple during these periods.

• Surge in phishing and spoofing: Holiday-themed phishing spikes—email campaigns impersonating retailers, shipping updates, or gift-giving urgencies—can increase by 300–400% 2.

• Transaction noise: With transaction volumes up 300–500%, fraudulent activities often blend with legitimate traffic  2.

• Automation and AI misuse: Cybercriminals now deploy AI-driven scams and cloned websites to accelerate data theft 34.

Notable Holiday-Season Attacks

1. Target (Nov 2013)

A massive breach during Thanksgiving weekend exposed 40 million credit/debit card numbers and 70 million customer records. The fallout: over $18.5 million settled and enduring reputational damage 56.

2. Macy’s Magecart Breach (Nov 2019)

Just ahead of Black Friday, attackers injected card-skimming JavaScript into Macy’s checkout system. Thousands of card details were compromised—undermining trust during the peak holiday sale period 7.

3. San Francisco Muni Ransomware (Nov 2016)

During Thanksgiving weekend, the Muni transit system was hit with “Mamba” ransomware. Over 2,000 systems were encrypted, fares couldn’t be processed, and the agency faced service disruptions for 700,000+ daily riders 7.

4. Staples Ransomware (Cyber Week 2023)

Retail giant Staples suffered a ransomware attack amid peak retail season. Though financial details weren’t publicly disclosed, the timing severely affected supply-chain operations and sales flow 8.

5. Orion S.A. Business Email Compromise (Dec 2024)

A European chemical manufacturer fell victim to a BEC scam: attackers impersonated internal communications and processed fraudulent wire transfers totaling ~$60 million—over half the company’s annual profits 5.

6. Healthcare Ransomware on Thanksgiving (2023)

Several U.S. hospitals hit on Thanksgiving Day had to divert emergency patients while recovering from ransomware—demonstrating how holiday attacks can impact critical services  98.

Key Lessons for Cybersecurity Leaders

• Reinforce off-hour coverage:

With 52–56% of ransomware attacks occurring during weekends or holidays, maintaining round-the-clock monitoring is essential 1011.

• Enforce financial safeguards

Require dual-approval and voice verification for year-end wire transfers and vendor banking changes critical defenses against BEC attacks like Orion’s.

• Rodust phishing training and filtering:

Deploy AI-based filters and regular training focused on seasonal scams—like fake shipping alerts and holiday promotions.

• Vet external code and gift-card policies:

Scrutinize third-party scripts on checkout pages and establish clear rules around gift-card requests to avoid Magecart and impersonation scams 125.

• Use proactive threat intelligence:

Monitor bulk domain registrations for keywords like “Black Friday,” “Christmas,” or “FlashSale”—over 18,000 holiday-themed domains were registered in 2025, with many being malicious 13.

• Leverage AI for defense:

While attackers use AI to spoof emails and spoof brands, defenders must also adopt AI-powered threat detection to analyze login patterns, domain anomalies, and user behavior in real time.

With Avocado Systems AI, your cyber resilience remains proactive, consistent, and effective—even when teams are at reduced capacity.

As the new year approaches, leaders must reinforce defenses and sharpen incident response during this high-risk window. By combining vigilance, policy, training, threat intelligence, and AI-powered security like Avocado, businesses can protect their customers, brand reputation, and bottom line.

Wishing you uninterrupted operations, a secure holiday season, and a prosperous New Year ahead!