Preparing Retailers for AI-Driven Cyber Threats Through the Holiday Season and Beyond

Cybercriminals follow consumer behavior, and the holiday season provides a prime opportunity. As shoppers continue to make purchases online and in-store, attackers are increasingly leveraging artificial intelligence tools to accelerate attacks, putting both consumers and retailers at risk.

To preserve consumer trust and protect brand reputations, retailers must safeguard against attacks that can compromise valuable data points, including personal and financial information. Many cyberattacks target critical endpoints such as point-of-sale (POS) systems, handheld scanners, mobile apps, or website transaction pages. Securing these access points is essential to maintaining safe and seamless shopping experiences throughout the season and beyond.

Where Retailers Are Most Vulnerable in the AI Era

Retail endpoints are valuable targets for cybercriminals. With high accessibility, frequent customer interactions, and constant connectivity, these systems provide attackers with opportunities not only to steal valuable data but also to infiltrate broader networks. A single compromised POS, for example, can disrupt checkout operations, skew inventory accuracy, or interfere with returns processing.

This risk becomes even more pronounced in retail environments where vulnerabilities are common,  including older POS operating systems and legacy in-store technologies; complex third-party integrations that connect mobile apps, loyalty platforms, payment systems, and e-commerce; and large, geographically dispersed networks of endpoints that are difficult to monitor consistently.

AI-Driven Attacks: What Retailers Should Expect

The stakes for retailers are continuing to rise through 2026 due to attackers’ use of AI tools. Attackers leverage automated scanning tools to identify unpatched vulnerabilities across exponentially more devices than any human can manually scan.

In addition, AI-generated malware can adapt to defenses, increasing the sophistication of these attacks. We also see attackers leveraging AI tools to automate and strengthen the quality of their phishing and social engineering campaigns, which often target store-level employees.

Why Traditional Patch Cycles Are No Longer Sufficient for Retailers

Patching is one of the most fundamental cybersecurity defenses — the process of identifying vulnerabilities and applying fixes to close security gaps before attackers exploit them. But traditional, manually driven patch cycles running every few months or only during planned maintenance windows are no longer adequate for today’s retail threat landscape.

Retailers face inherent patching challenges due to geographically distributed stores, limited maintenance windows, and a wide variety of in-store devices. From POS terminals to self-checkout kiosks, tablets and inventory scanners, this diversity creates operational friction that makes consistent, timely patching difficult.

These constraints give attackers more opportunity to exploit outdated systems, a problem amplified by AI tools that scan for vulnerabilities at unprecedented speed and scale. To counter this advantage, retailers must close the gap between detection and remediation, shifting from periodic patch cycles to continuous, automated patching that eliminates weaknesses before attackers can capitalize on them.

How Retailers Can Strengthen Their Security Posture by Turning to Autonomous Endpoint Management

Retailers can strengthen their security posture by shifting toward autonomous endpoint management, which blends automated remediation with human oversight. By centralizing visibility across stores, these systems can continuously detect vulnerabilities, apply patches, validate updates, and resolve issues at scale much quicker than manual processes allow.

Humans still guide policies, monitor exceptions, and safeguard operations, but automation handles the heavy lifting across diverse, aging and business-critical devices. This hybrid approach shrinks the window of vulnerability, reduces disruption during high-traffic periods, and ensures IT, security and store teams stay aligned without slowing down sales or customer experience.

Moving Forward: Building a More Resilient Retail Environment

AI-powered attacks are accelerating, but proactive preparation can curb risk. Modernizing endpoint protection now ensures peak shopping and returns seasons run smoothly. In the next era of retail security, resilience, speed and real-time visibility will determine which companies stay protected and operational.

Chaz Spahn is the director of product management at Adaptiva, a global leader in autonomous endpoint management.