Wilkens: How cybersecurity defense is changing for fleets and transportation

For decades, cybersecurity defense has relied on a standard blueprint: Build a perimeter, guard the perimeter, hope the perimeter holds. Firewalls, antivirus tools, and annual compliance checklists form the backbone of many organizations’ strategies.

But attackers have matured, operations have changed, and the perimeter has disappeared. This means that the transportation sector now finds itself in a threat landscape that is far too dynamic for traditional defenses to handle.

Effective cybersecurity defense now requires an adaptive, intelligence-driven, whole-of-business approach. Understanding this isn’t optional; it’s a prerequisite for resilience.

Traditional perimeter security no longer shields fleets from modern cyberthreats

Early cybersecurity strategy was simple, predictable, and built around the assumption that threats were unsophisticated and generalized in their targeting. They also assumed that these threats were going to originate from outside the organization’s well-defended perimeter. The focus, therefore, was on keeping the bad guys outside the walls.

For years, organizations tolerated flat network designs, relied on signature-based antivirus to block known malware, and were built around perimeter-based models that assumed internal systems were inherently trustworthy.

This approach worked when attackers cast wide nets, tools evolved slowly, and business systems were primarily on-premises vs. cloud-hosted and not universally interconnected via application programming interfaces (APIs).

The rapid and ongoing growth and evolution of operations, identity systems, cloud environments, mobile workflows, and third-party integrations means that traditional defenses now leave massive blind spots that increasingly sophisticated adversaries aggressively exploit.

Fleet cybersecurity must adapt to AI, automation, and specialized attack tactics 

Just as social engineering evolved into precision-targeted, artificial intelligence (AI)-crafted deception, awareness training had to evolve with it. A similar change has taken place in the broader cybersecurity defense model. Modern attackers don’t “hack in” as much as they log in. They use legitimate tools, stolen credentials, and AI-assisted reconnaissance to move faster than human defenders can respond.

Response windows are shrinking, attack surfaces are expanding, and adversaries are increasingly operating like full-scale enterprises.

Today, fleets aren’t defending against a single intrusion tactic. They’re defending against:

• Identity compromise at scale;
• API abuse and cloud misconfiguration;
• Weaponized remote management tools;
• Supply-chain trust exploitation;
• AI-generated deception and deepfakes;
• Cyber-enabled cargo theft; and
• Modular, specialized criminal networks working in coordinated roles.

Defense has become less about preventing every possible intrusion and more about assuming a breach has occurred, detecting anomalies quickly, isolating impacted systems effectively, responding decisively, and recovering reliably.

Integrating cyber, physical, and operational security for fleet resilience

One of the clearest patterns shaping modern defense is the disappearance of boundaries between traditionally siloed security disciplines. Cyber intrusion now routinely drives physical theft. Operational disruptions now stem from digital fraud. Third-party software compromises now cascade across entire industries. Cybersecurity, operational security, and physical security can no longer be considered in isolation from each another; they are each parts of the same whole.

Effective defense today looks less like a well-guarded fortress and more like a layered, tightly integrated web of controls. The perimeter is no longer the edge of the enterprise network. The perimeter is now every data asset, every device that accesses company resources, every employee, and every digital identity (human and non-human).

Building fleetwide cyber resilience boosts operations and protects revenue

The next stage of cybersecurity defense is already emerging, and fleets that adapt quickly will find themselves not only safer—but operationally stronger.

What does future-ready defense look like?

Continuous verification 

Users, systems, devices, APIs, vendors—everyone must continuously prove their trustworthiness, not just at login or onboarding.

Intelligence 

Threat intelligence sharing, operational telemetry, and real-time anomaly detection are becoming the backbone of transportation cybersecurity.

Governance

Regulatory expectations are rising, from incident reporting to data protection to secure-by-design requirements for vendors.

Culture

Security-aware operations outperform compliance-driven ones every time. Organizations that normalize verification, reporting, and security-first thinking will outpace those that rely solely on tools.

Convergence

Cyber, physical, and operational security will be treated as interdependent layers of the same mission: protecting people, freight, revenue, and trust.

Cybersecurity defense has evolved from firewalls and antivirus into a fully integrated discipline that spans every function of the modern fleet. In this new environment, attackers collaborate, attackers specialize, attackers automate, attackers move at machine speed. Defenders must do the same.