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The cybersecurity landscape is entering a year defined by acceleration. AI adoption is moving faster than governance models can keep up. Adversaries are using generative tooling to scale attacks. And connected devices, from industrial systems to life-critical medical equipment, are blurring the line between digital compromise and real-world consequences.

Security has long operated as an integrated partner across the business, but 2026 will raise the stakes. The challenge will be matching the accelerating speed of AI adoption, attacker innovation, and connected-system risk. Our predictions reveal how macro forces will cascade downward to reshape executive decisions, defensive models, testing disciplines, and specialized domains.

Pen Testing Isn’t Dying, It’s Multiplying.

Every year, someone calls time of death on pen testing. They’ve been wrong for twenty years, and they’ll still be wrong in 2026. Hey, at least they're consistent. As the attack surface grows and adversaries move faster, testing is needed more often, not less. Proactive testing will be delivered both continuous and point in time to help people understand their security posture. Just like your Apple Watch doesn’t replace your annual checkup, new tech won’t replace expert testing. It’ll just make it smarter and more available.

For CISOs, AI Is Now an Irreversible Data Risk Decision

For CISOs, AI Is Now an Irreversible Data Risk Decision In 2026, CISOs will face a shift from experimenting with AI to operating in a world where adoption is no longer optional. Businesses will pursue AI for efficiency, capability, and competitive pressure, often faster than security teams can evaluate the risks. CISOs won’t be the arbiters of which AI initiatives move forward, but they will be accountable for how safely they do. The real challenge will be mitigating against a growing layer of shadow AI, trying to monitor user usage, evaluating AI adoption against unclear cost models, and analyzing increasingly complex data-sharing across vendors and models. The CISO’s role will center on enabling the business while mitigating risks at a pace that matches AI’s acceleration, guiding organizations through decisions that may prove irreversible.

Medical Devices Will Drive a Surge in Specialized Hardware Testing

As the line between the physical and digital worlds disappears, connected hardware, especially critical devices in sectors like healthcare, is introducing unprecedented physical-world risk. For example, the updated FDA requirements taking effect in 2026, includes new quality-system expectations for design controls, risk management, and cybersecurity. With this, medical-device manufacturers will face stronger scrutiny of how their products are engineered and secured. These shifts will force a dramatic increase in specialized hardware and product testing, moving beyond simple network assessments. This deeper security focus is essential for embedded systems, radio technology, and industrial components, where even a minor flaw can have catastrophic safety or physical consequences. Companies will be compelled to invest in expertise capable of managing liability and risk across their entire fleet of connected devices, making comprehensive hardware security a non-negotiable requirement.

AI Will Drive the Rise of Specialized Red Teams

As AI reshapes both enterprise environments and attacker capabilities, Red Teams will be forced to evolve in kind. AI-driven systems are now woven into everyday business operations, creating new and often poorly understood attack paths. At the same time, adversaries are already using generative models to map environments faster, craft sharper social engineering pretexts, and produce deepfakes of executives and trusted stakeholders. In 2026, this shift will accelerate the move toward highly specialized Red Teams, i.e., dedicated groups focused on OT, AI systems, business processes, and other niche attack surfaces. Organizations will recognize that generic testing can’t keep pace with AI-enabled threats, and tailored Red Teams will become essential to uncovering the risks hiding in these rapidly expanding domains.

AI Weaponization Will Force a New Era of Test Co-pilots for Defense

We’re entering an AI vs. AI arms race. Attackers are already using generative models to automate vulnerability discovery and scale their operations. That’s not theory. It’s happening now. Defensive teams that don’t adapt will get buried in volume and speed. The right answer isn’t to replace people with machines. It’s to pair them. AI can crunch through the repetitive groundwork, but humans still have to decide what’s real, what’s exploitable, and what actually matters. Think of it as a test co-pilot: automation handles the heavy lifting, and the tester focuses on creative, high-impact work. The future of security testing will depend on who can use AI more effectively, and human direction will remain the difference between running scans and actually breaking systems.

2026 Will Demand Speed, Depth, and Adaptability

2026 won’t reward hesitation. It will reward clarity, prioritization, and a willingness to rethink long-standing assumptions about how security teams operate. Leaders should prepare for faster decision cycles, more specialized testing demands, and an environment where AI-driven systems need continuous scrutiny. The path forward starts with understanding your highest-impact risks and investing in the expertise required to uncover and validate them.

If you’re preparing your team for this next chapter or evaluating how your testing strategy needs to adapt, we’re always here to compare notes, share what we’re seeing, and help you build a plan that meets the moment.

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About the author, Vincent Liu

CEO & Co-founder of Bishop Fox

Vincent Liu (CISSP) is CEO and cofounder at Bishop Fox. With over two decades of experience, Vincent is an expert in offensive security and security strategy; at Bishop Fox, he leads firm strategy and oversees client relationships. Vincent is regularly cited and interviewed by media such as Al Jazeera, The Information, and NPR while also writing as a contributing columnist for Dark Reading. He has presented at Microsoft BlueHat and Black Hat and has co authored seven books including Hacking Exposed Wireless and Hacking Exposed Web Applications. Vincent sits on the advisory boards of AppOmni, Elevate Security, Mod N Labs, and the University of Advancing Technology in addition to serving as returning faculty at the Practising Law Institute. Prior to founding Bishop Fox, Vincent led the Attack & Penetration team for the Global Security unit at Honeywell International. Before that, he was a consultant with the Ernst & Young Advanced Security Centers and an analyst at the National Security Agency.
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Bfx25 Christie Terrill Update Bio

About the author, Christie Terrill

Chief Information Security Officer

Christie Terrill is the Chief Information Security Officer (CISO) of Bishop Fox, with more than 20 years of experience in security and technology services. She oversees the company’s security strategy and program, and has played an integral part in developing the company’s operational strategy while simultaneously ensuring the greatest value for clients. A 15-year Bishop Fox veteran, Christie most recently drove the rigorous, multi-year process of completing certifications for Bishop Fox’s ISO/IEC 27001 Type 2 and SOC 2 Type 2 Security Trust Services Criteria. Having joined Bishop Fox as a consultant, she quickly ascended to partner and established the company's enterprise security consulting practice, as well as serving in the sales organization.

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About the author, Kelly Albrink

Vice President of Delivery, Consulting Security Services

Kelly Albrink (CCNA CyberOps, GCIH, GSEC, OSCP, GWAPT, Sec+) is the Vice President of Delivery for Consulting Security Services at Bishop Fox. In this role, she oversees the delivery of comprehensive security assessments including red teaming, application penetration testing, cloud penetration testing, network penetration testing, and hardware (IoT) security services.

Kelly has presented at numerous Bay Area security events including Okta's inaugural security conference, Okta Rex, Day of Shecurity, and the DeadDrop San Francisco Meetup. She is a recipient of the SANS CyberTalent Immersion Academy scholarship and is an active CTF participant. Kelly has competed in the NetWars Tournament of Champions, a national invite-only competition that admits only those who have placed highly in regional CTFs. As a consultant, Kelly frequently performed hardware and wireless testing, becoming a subject matter expert in this area. She is responsible for identifying a high-risk CVE that impacted an Eaton power management appliance. As the Application Security Practice Director at Bishop Fox, she has helped facilitate the expansion of the practice to focus on security during the design phase. This includes the development of offerings such as architecture security assessments, source code review, and threat modeling. She has also created a consulting mentorship program and led the revamp of an internal knowledge-sharing series of technical talks.

Beyond her professional responsibilities, Kelly is an active member of the security community. She volunteers with her local hackerspace, Noisebridge, where she organizes Infosec Lab Nights and mentors aspiring penetration testers. She holds multiple industry certifications including OSCP, GWAPT, GCIH, GSEC, CCNA CyberOps, and Security+, demonstrating her commitment to continuous learning and professional development in cybersecurity. At the first ever DerpCon, she presented on Software Defined Radio (SDR), a topic she later wrote about for the Bishop Fox blog in "Ham Hacks: Breaking into Software-Defined Radio."

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Trevin Edgeworth

About the author, Trevin Edgeworth

Red Team Practice Director

Trevin Edgeworth is the Red Team Practice Director at Bishop Fox, where he focuses on building and leading best-in-class adversary emulation services to help customers of all sizes and industries strengthen their defenses against current and emerging threats.

Trevin has over 20 years of security experience; he has built and overseen red team programs for several Fortune 500 companies, including American Express, Capital One Financial, and Symantec Corporation. Other accomplishments include leading a security organization as Chief Security Officer (CSO) for a major security company. Trevin has led a variety of security functions in his career, including cyber threat intelligence, hunt, deception, insider threat, and others.

Trevin is an active member of the security community. He has presented at several industry conferences and been interviewed by leading publications on topics such as red teaming and threat intelligence.

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About the author, Dan Petro

Senior Security Engineer

As a senior security engineer for the Bishop Fox Capability Development team, Dan builds hacker tools, focusing on attack surface discovery. Dan has extensive experience with application penetration testing (static and dynamic), product security reviews, network penetration testing (external and internal), and cryptographic analysis. He has presented at several Black Hats and DEF CONs on topics such as hacking smart safes, hijacking Google Chromecasts, and weaponizing AI. Dan holds both a Bachelor of Science and a Master of Science in Computer Science from Arizona State University.

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