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In a recent Fireside Chat, Bruce Schneier- renowned cryptographer, Harvard professor, and one of the most influential voices in cybersecurity- joined Bikash Barai, Founder & CEO of FireCompass, to discuss how AI is fundamentally reshaping pentesting, red teaming, and the future of cyber defense.
Watch the Full Fireside Chat Recording
Gain first-hand insights from Bruce Schneier and Bikash Barai on how AI is redefining offensive security, pen testing, and cyber defense strategies: Link
Hacking, AI, and the Changing Nature of Security
Bruce began with a foundational perspective: hacking is fundamentally “following the letter of the law while breaking the spirit of it.”
He noted that every system of rules- technical, social, legal, or economic- contains loopholes that can be exploited. This makes “hacking” much broader than software intrusion; it applies to tax codes, political frameworks, and day-to-day human systems.
“Our society is filled with systems of rules, and people have been hacking them for centuries.”
AI now introduces new dynamics in how such systems are both exploited and defended.
The Four S’s: How AI Surpasses Human Capabilities
Drawing from his latest book Rewiring Democracy, Bruce outlined four dimensions in which AI can excel beyond human performance:
1. Speed
AI operates at machine speed, reacting and analyzing far faster than humans.
2. Scale
Tasks that once required large teams- such as influence campaigns—can now be executed by one person with thousands of AI-driven agents.
3. Scope
Models can function across many domains simultaneously, even if not perfectly specialized.
4. Sophistication
AI can hold and process far more variables than a human mind, enabling it to identify patterns and opportunities that experts may miss.
Applied to pen testing, these dimensions reveal why the field is “ripe for revolution.”
Pen testing: A Human-Centric Field Meets Machine Intelligence
Historically, pen testing has been manual, experiential, and intuition-driven.
But as Bikash highlighted:
“What took humans days or weeks, AI can now attempt in minutes—across a much larger attack surface.”
FireCompass routinely benchmarks human pentesters against its AI agents. The shift has been rapid:
Day 1: AI 7 – Humans 0
Day 2: AI 9 – Humans 2
A year ago, AI could perform only 60-70% of what an experienced human could. Today, it is approaching near-complete parity, and in several areas, surpassing human teams.
Bruce echoed this broader trend: both attackers and defenders are increasingly relying on AI to automate vulnerability discovery and exploitation.
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A Rapidly Widening AI Divide
Bikash pointed out a structural concern:
- 90% of enterprises still conduct annual pentests.
- These assess only ~20% of the attack surface.
- They are typically narrow-scope, external-only, and do not model multi-stage attack paths.
Meanwhile, threat actors are adopting AI faster than defenders can integrate it.
Bruce summarized the risk:
“Short term, we’re in for dangerous times. Attackers are more agile.”
Over the long term, however, he believes defenders will ultimately benefit more as AI becomes part of compilers, scanners, and development tools-creating the possibility of almost real-time vulnerability discovery and remediation.
Continuous Pen testing: A Shift in Kind, Not Just Degree
Both speakers agreed that continuous, AI-driven pen testing is not merely a faster version of the traditional approach.
Bruce framed it as a structural shift:
A change in degree becomes a change in kind.
When pen testing becomes:
- continuous
- autonomous
- event-triggered
- scalable across entire digital estates
…it becomes a fundamentally different discipline, no longer constrained by human bandwidth or cadence.
Bikash added that FireCompass’ AI doesn’t compute static attack graphs; instead, it creates and executes attack paths dynamically using reasoning-based models-a capability that was impossible even a decade ago.
The Rise of Non-Determinism in Cybersecurity
LLMs introduce a level of unpredictability-sometimes an advantage, sometimes a challenge.
Bruce noted:
“It can miss something-but it can also find things humans never imagined.”
This mirrors creative human intuition more closely than traditional rule-based systems.
The result: previously unseen exploitation paths and new forms of defensive reasoning.
Will AI Assist Pen testers – Or Replace Them?
This question sparked one of the most thought-provoking parts of the discussion.
Bikash suggested:
- The traditional pen tester role is shifting.
- Roles requiring checklist execution will be automated.
- Future professionals will focus on creative reasoning, first-principles thinking, and understanding complex context.
Bruce added that context—not prompting—is the emerging frontier.
Humans intuitively understand context; AI currently does not.
Organizations that succeed will likely be those that build rich contextual layers around AI systems.
Conclusion: A New Era of Cybersecurity Has Already Begun
The session reinforced a central truth:
AI is no longer an enhancement to pen testing—it is becoming the primary engine of both attack and defense.
Bruce noted:
“Security will soon become a self-modifying ecosystem-living, adapting, evolving in real time.”
Bikash added:
“We’re moving from the stone age to the metal age of cybersecurity.”
Tools, processes, and job roles are undergoing generational change.
Organizations that adapt early will be better positioned to navigate the rapidly expanding AI-driven threat landscape.
