Securing Retail’s Trillion-Dollar Season: How Cybercriminals Exploit Peak Holiday Pressure

In early November, the National Retail Federation projected that holiday sales would exceed $1 trillion — a staggering figure that reinforces why the final weeks of the year remain the most critical revenue window for retailers.

Cybercriminals know this better than anyone. Threat actors routinely time attacks to exploit the perfect storm of holiday season pressures: record transaction volume, operational urgency, strained IT resources, and the absolute necessity of uninterrupted uptime. From ransomware and data exfiltration campaigns to credential theft and account takeovers, attacks reliably surge during the period when retailers can least afford disruption. 

Complicating matters further, retailers are now confronting a new wave of AI-driven and automated cyber threats. According to the Retail & Hospitality Information Sharing and Analysis Center’s 2025 Holiday Season Cyber Threat Trends report, organizations should expect a surge in sophisticated automated bot attacks timed to coincide with peak seasonal shopping periods.

In this new reality, retailers must prepare for an entirely new level of speed, sophistication, and persistence in cyberattacks.

Awareness Is the First Step

For retailers, education and awareness remain the most effective early defenses against holiday season cybercrime. You can’t protect what you don’t understand, and during a time when both consumer activity and adversary operations surge, visibility into potential threats and common attack patterns becomes indispensable. 

Building that awareness starts with understanding the tactics adversaries rely on during high-traffic periods. Below are three of the most common and damaging attacks facing retailers during the holiday rush:

1. Ransomware and Data Exfiltration

Knowing retailers are under immense pressure to maintain flawless uptime, attackers often deploy ransomware or data theft operations immediately before major sales events, when downtime would be most catastrophic.

Modern extortion campaigns frequently combine encryption with large-scale data exfiltration to maximize leverage. Forced to choose between business continuity and financial loss, retailers may find the cost of downtime far exceeding the ransom itself. Under these conditions, attackers gain extraordinary bargaining power, making seasonal extortion one of the most damaging and disruptive threats retailers face.

2. Fraudulent Supplier and Shipping Notices 

Retailers are also contending with a surge in AI-generated phishing and social-engineering scams that impersonate core business processes, with a goal to exploit customer loyalty and erode brand trust. 

Threat actors now use generative AI (genAI) to craft fraudulent supplier invoices, shipping updates, refund alerts, and support messages that closely mimic legitimate communications in tone, format, and branding. Because these messages appear polished, contextually relevant, and grammatically flawless, they increasingly bypass traditional phishing filters and can trick even vigilant recipients into clicking, paying, or sharing sensitive information.

Modern adversaries also leverage multi‑modal genAI, which is capable of synthesizing not just text but also voice and image content, to convincingly mimic customer service representatives or logistics partners. This makes real‑time impersonation via chat, email, phone, or both scalable and persuasive, underscoring the need for layered verification and adaptive filtering beyond text‑only detection defenses.

3. Credential Exploitation and Account Takeovers 

Attackers are aggressively targeting customer accounts by reusing or purchasing stolen login credentials at scale. Retail accounts packed with stored payment cards, loyalty points, and gift-card balances offer quick and profitable opportunities for exploitation.

One rapidly growing tactic is gift card draining, a low-effort, high-yield method that allows attackers to quietly monetize stolen access with minimal detection. Because these intrusions often unfold quietly within authenticated user sessions, strong observability, behavioral analytics, and anomaly identification are essential to catching unusual patterns before they erode customer confidence and brand reputation.

Beyond individual credential theft, retailers are also facing an escalation in bot‑driven credential‑stuffing and API‑abuse attacks. Automated bots continuously test stolen usernames across loyalty apps, promo systems, and payment APIs to exploit weak password reuse and poorly monitored endpoints. These attacks can occur at a scale and a speed beyond human monitoring, leading to account lockouts, fraudulent purchases, and lost revenue. Tight API authentication, intelligent rate‑limiting, and credential monitoring services are now essential for mitigating this form of automated fraud.

By equipping every level of the retail organization — from executive leadership to frontline staff — with timely intelligence on active threats and common attack vectors, retailers can spot warning signs earlier, make faster and more informed decisions, and shrink the window of opportunity for attackers during peak season.

5 Recommendations to Strengthen Retail Cyber Resilience

With clearer visibility and current threat intelligence, retailers can move from awareness to action, building the operational resilience needed to protect both revenue and customer trust during peak trading periods. The following recommendations outline the foundational steps for preventing, detecting, and responding to holiday season attacks. 

Incident Readiness 

Preparation is everything during the holidays. Conduct tabletop exercises well before peak season to test, refine, and validate incident response plans, clarify roles, and confirm that escalation paths are understood across leadership, IT, security, and customer facing teams. Ensure:

• Security tooling is properly configured and actively monitored.
• Backups are recent with appropriate retention policies, tested and protected against threats including immutable storage.
• Response playbooks reflect real-world ransomware, phishing and account takeover scenarios.
• Decision making authority is clearly defined for high-pressure situations.

Frequent, realistic practice reduces uncertainty and accelerates response when minutes matter.

Exposure Management 

Attackers target what’s exposed, and retail environments have a wide footprint. Continuously inventory and evaluate all externally facing assets, including web portals, APIs, cloud applications, point-of-sale (POS) integrations, and remote-access systems. Prioritize remediation based on exploitability, asset criticality and business impact. Pay particular attention to end-of-life systems, legacy infrastructure and seasonal workloads that may not receive regular patching. 

Proactive attack surface reduction dramatically lowers the attacker's options.

Social Engineering Preparation 

Peak season stress creates the perfect conditions for human error, which is exactly what attackers exploit. Reinforce a “Pause → Verify → Act” mindset across the organization. Employees should be encouraged to slow down before clicking links, processing refunds, approving invoices or responding to urgent requests. Key steps include:

• Regular phishing simulations tailored to retail-specific lures.
• Training on manipulation tactics (urgency, authority, impersonation).
• Clear verification processes using secondary, trusted communication channels.
• Helpdesk protocols for validating password resets and access requests.

A calm, verification-first culture significantly reduces the risk of AI-enhanced social engineering campaigns. 

Managed Detection and Response 

Real-time detection and response are essential when attackers move fast and retailers cannot afford downtime. Ensure continuous monitoring across endpoints, POS and retail business systems, and eCommerce platforms.

Take advantage of genAI as a force‑multiplier for threat detection and response, using machine learning and behavioral analytics to triage alerts, correlate indicators, and automate containment. When paired with playbook‑driven orchestration, AI accelerates investigation while ensuring threats are neutralized before they escalate into business disrupting incidents.

Vendor and Supply Chain Risk Controls 

Holiday operations depend on a complex ecosystem of external partners. Reassess third-party risks by validating:

• Access controls and least-privilege permissions.
• Security posture for shipping, payment and IT vendors.
• Incident notification requirements within contracts.
• Data handling policies and integration security standards.

A compromised partner can be a direct path into retail systems, making supply chain due diligence an essential layer of defense.

The Bottom Line

The holiday rush is more than a stress test for sales, it’s a stress test for cyber resilience.

Retailers that follow the above roadmap can safeguard their business, protect customer trust and maintain operational confidence when the stakes are highest.