Securing Your Business During the Holiday Season

The holiday season is the most profitable time of year for many businesses — and for cybercriminals. Between November and January, organizations face a convergence of factors that dramatically increase their exposure to cyberattacks: reduced staffing, higher transaction volumes, urgent deadlines, and employees distracted by personal shopping and travel. Attackers understand these dynamics intimately and time their campaigns to exploit the exact period when defenses are weakest and the pressure to keep systems running is highest.

Why Holidays Create a Perfect Storm for Cyber Threats

Several factors compound during holiday periods to create conditions that attackers actively exploit. IT teams operate with skeleton crews as staff take vacation time, meaning fewer eyes on security alerts and longer response times when incidents occur. The Cybersecurity and Infrastructure Security Agency has repeatedly issued advisories warning organizations to remain vigilant during holidays and weekends, noting that threat actors have historically launched some of their most damaging attacks during these periods.

Transaction volumes spike across retail, e-commerce, financial services, and logistics. Every additional transaction is another opportunity for fraud, and the sheer volume makes it harder for automated systems and human reviewers to distinguish legitimate activity from malicious behavior. Employees processing purchase orders, invoices, and wire transfers under holiday deadlines are more likely to approve requests without the scrutiny they would apply during a normal workweek.

The urgency factor cannot be overstated. When a CFO receives an email requesting an emergency wire transfer on December 23rd, the instinct is to process it quickly before the office closes rather than spend an hour verifying its authenticity. Attackers craft their social engineering campaigns around exactly this kind of pressure.

Holiday Phishing Campaigns

Phishing attacks increase significantly during the holiday season, and the lures become more convincing because they align with what people expect to receive. Shipping notifications from carriers like UPS, FedEx, and USPS are standard phishing templates year-round, but during the holidays they become far more effective because nearly everyone is expecting packages. An employee who would normally scrutinize an unexpected delivery notification in March will click through without hesitation in December.

Holiday-themed phishing extends well beyond shipping notifications. Attackers send fake charity solicitation emails, fraudulent gift card offers, bogus travel deal confirmations, and counterfeit retailer promotions. These messages often replicate the branding of well-known companies with remarkable accuracy and direct recipients to credential-harvesting sites or pages that deploy malware. The Anti-Phishing Working Group has documented consistent year-over-year increases in phishing activity during the fourth quarter, with attacks peaking in the weeks surrounding major shopping events like Black Friday and Cyber Monday.

Business email compromise takes on additional dimensions during the holidays. Attackers impersonate executives who are known to be traveling or on vacation, sending urgent requests to subordinates who are reluctant to delay action when the boss appears to need something handled immediately. The absence of the impersonated executive makes verification harder, and the cultural expectation of availability during the holidays makes the target less likely to question the request.

Ransomware Timing Is Not Coincidental

The timing of major ransomware attacks correlates heavily with holidays and weekends. The Colonial Pipeline attack occurred over Mother’s Day weekend. The Kaseya supply chain attack was launched on the Friday before Independence Day. The JBS meat processing attack hit over Memorial Day weekend. These are not coincidences. Ransomware operators deliberately choose periods when incident response capabilities are degraded, knowing that the combination of reduced staffing and increased pressure to restore operations quickly makes organizations more likely to pay.

During the holiday season, this dynamic is amplified. A retailer hit with ransomware on Black Friday faces the prospect of losing its most profitable sales days of the entire year. A logistics company locked out of its systems during peak shipping season risks contractual penalties, customer defections, and cascading delays across its supply chain. The calculus of paying versus suffering operational losses shifts dramatically in the attacker’s favor when every hour of downtime carries outsized financial consequences.

Smaller businesses are particularly vulnerable because they often lack the redundancy and incident response capabilities to recover quickly. A mid-sized retailer without tested offline procedures and current backups may face a choice between paying the ransom and closing for the season.

E-Commerce and Payment Fraud

Businesses that process online payments face heightened fraud risk during the holidays. Card-not-present fraud increases as transaction volumes grow, and the speed at which orders must be fulfilled creates pressure to reduce fraud screening that might slow down legitimate purchases. Attackers exploit this tension by making fraudulent purchases they know will receive less scrutiny during peak periods.

Gift card fraud is a particularly acute holiday threat. Attackers compromise gift card systems to steal balances before legitimate recipients can use them, or they use business email compromise to convince employees to purchase gift cards as supposed employee rewards or client gifts. The Federal Trade Commission has highlighted gift card scams as one of the most prevalent holiday fraud vectors, noting that losses run into hundreds of millions of dollars annually.

Website skimming attacks, where malicious code is injected into checkout pages to harvest payment card data in real-time, also intensify during peak shopping periods. Attackers target e-commerce platforms knowing that higher traffic means more card numbers captured per day, and that site owners may be reluctant to take their storefront offline for security remediation during the busiest sales period of the year.

Protecting Your Business Through the Season

Effective holiday security requires preparation that begins well before the season starts. Organizations should conduct a security review at least six weeks before their peak period, addressing patching, access controls, backup verification, and incident response readiness. Waiting until December to think about holiday security is already too late.

Staffing is the most critical factor. Ensure that security monitoring coverage does not drop during holiday periods, even if that requires engaging a managed security service provider to supplement internal teams. Establish clear on-call rotations with defined escalation procedures so that alerts received at 2 AM on Christmas Day reach someone who can act on them. Pre-authorize key incident response decisions so that the on-call team can contain a breach without waiting for executives who may be unreachable.

Implement additional verification procedures for financial transactions during the holiday period. Any wire transfer request, vendor payment change, or gift card purchase above a defined threshold should require out-of-band confirmation through a phone call to a known number — not a number provided in the email requesting the transfer. This single control prevents the majority of business email compromise losses.

Reinforce employee awareness with targeted, timely security reminders. A brief, focused message about holiday phishing threats sent the week before Thanksgiving will have more impact than annual security training completed months earlier. Focus on specific, actionable guidance: verify shipping notifications by going directly to the carrier’s website rather than clicking email links, confirm any unusual financial requests by phone, and report suspicious emails even if uncertain.

Technical Controls That Matter Most

Certain technical measures provide disproportionate protection during high-risk periods. Ensure multi-factor authentication is enforced on all remote access, email, and financial systems with no exceptions. Review and tighten conditional access policies to require additional verification for logins from unusual locations or devices, which is particularly relevant when employees access systems while traveling for the holidays.

Verify that endpoint detection and response tools are deployed, updated, and actively monitored across all systems. Confirm that backups are current, tested, and stored in a location that ransomware cannot reach from the production network. Pre-stage your incident response plan with contact information for legal counsel, cyber insurance carriers, forensic investigators, and law enforcement so that the first hours of a holiday incident are not consumed by searching for phone numbers.

Freeze non-essential changes to production systems during peak periods. Code deployments, infrastructure changes, and configuration modifications introduce risk and should be deferred until the holiday period ends unless they address an active security issue. This reduces the attack surface and eliminates the possibility that a rushed change creates an unintended vulnerability at the worst possible time.

After the Holidays

The risk does not end when the decorations come down. January brings its own threats as employees return to overflowing inboxes and may rush through messages without adequate scrutiny. Tax season phishing begins almost immediately, with fraudulent W-2 requests and fake IRS communications targeting both individuals and payroll departments. Conduct a post-holiday security review to assess whether any indicators of compromise were missed during the peak period and to identify improvements for the next cycle.

Organizations that treat holiday security as a seasonal project rather than a point-in-time effort build resilience that compounds over time. Each year’s lessons inform the next year’s preparations, and the muscle memory developed through regular incident response exercises ensures that when an attack comes — during the holidays or any other time — the response is swift, coordinated, and effective.

The holiday season should be a time of growth and celebration for your business, not a period of heightened vulnerability. Proactive preparation, vigilant monitoring, and clear procedures can dramatically reduce your risk. Contact We Solve Problems to build a security posture that protects your business year-round, including during the periods when attackers are most aggressive.