Interview with Kara Sprague - The AI Fix for Infrastructure's Oldest Security Risks.

Critical infrastructure, often built on decades-old systems and legacy code, remains vulnerable to cyberattacks. From pipelines and energy grids to transportation networks, we break down where critical infrastructure is vulnerable and how AI could potentially help strengthen defenses.

Interview with Mike Privette - The State of the Cybersecurity Market

Here at ESW, we use Mike Privette's Security, Funded newsletter to prepare for every news segment. His newsletter covers the latest fundings, acquisitions, public market performance, layoffs, and other pertinent market details every week. We particularly enjoy the weekly Vibe Check.

In this interview, he joins us for the third year in a row, to discuss the most interesting insights from his annual State of Market Report.

Post recording Adrian here: Whooooo, so this conversation was SO good, I decided to punt the news segment in favor of a part 2 with Mike, so enjoy!

Also, though I punted the news segment, I did collect these stories and annotated them, so I think there's still some value in leaving them in the show notes. Scroll down for the links and my comments on each of these!

Weekly Enterprise News

Finally, in the enterprise security news,

1. funding announcements seem to be ramping up before RSA
2. Should security architects be shifting right?
3. How McKinsley's AI platform got hacked… by AI
4. Amazon is having a bad time with AI lately
5. Europe announces a Google Workspace/Microsoft 365 replacement
6. Robot dogs are apparently guarding datacenters now
7. Some much needed security humor in our squirrel stories before we all fly to San Francisco and lose our minds for a week

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-451

Interview with Jeremy Snyder from FireTail about AI Governance

Death by a thousand cuts: the AI shadow IT problem

I think the best description of the AI governance problem during this interview was the title of the award-winning movie, Everything, Everywhere, All At Once. Generative AI has been disrupting businesses, products, and vendor risk management for a few years now. FireTail is one of the companies trying to address this problem for enterprises, so we check in with Jeremy Snyder to see how things are going.

Segment 1 Resources:

• https://www.firetail.ai/ai-breach-tracker

Interview with Allie Mellen about her new book, Code War: How Nations Hack, Spy, and Shape the Digital Battlefield

We're VERY excited to check out Allie's new book, which will be released on St. Patrick's Day 2026! The timing could not be better, as her book is perfectly positioned to provide some much needed perspective on the cyber aspects of the ongoing war in Iran.

Is it normal to see the use of wipers on healthcare companies in the midst of the conflict? Is there any precedent for hyperscaler datacenters getting targeted (some of AWS's EMEA regions are still recovering)? Check out the conversation to find out!

Pick up the book!

• from Wiley
• from Barnes & Noble
• from Amazon
• Allie's personal website

The Weekly Enterprise News

Finally, in the enterprise security news,

1. Vibes and funding!
2. Starting to see some disruption in the vuln mgmt space (finally!)
3. Tons of new free tools
4. lots of essays
5. lots of reports
6. logs of breaches
7. the talks our hosts are giving at RSAC conference
8. and someone is selling an actual cone of silence???

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-450

Interview with Anna Pham

Breaking in with ClickFix: Anatomy of a modern endpoint attack

Cybersecurity company Huntress just published a report on a new ClickFix variant they've discovered, which they've dubbed CrashFix. This technique was developed by KongTuke to serve as the primary lure within a new custom malicious browser extension also created by the group.

In short, the team observed the threat actors using KongTuke's malicious browser extension to display a fake security warning, claiming the browser had "stopped abnormally" and prompting users to run a "scan" to remediate the threats. Upon "running the scan," the user is presented with a fake "Security issues detected" alert and instructed to manually "fix" the issue by opening the Windows Run dialog, pasting from their clipboard, and pressing Enter.

The malicious extension silently copies a PowerShell command to the clipboard, disguised as a legitimate repair command. From there, they execute the malicious command.

Segment Resources:

• BLOG - Dissecting CrashFix: KongTuke's New Toy

Interview with David Zendzian

Continuous compliance and real security lifecycle management

Supply chain attacks are not just on the rise; attackers are learning from the past, making these attacks even more effective and dangerous than before. It was just over a month ago when the Shai-Hulud attack first impacted NPM packages, forcing enterprises around the world into lockdown. While only 187 packages were compromised in that initial incident, it served as a wake-up call for many: an accurate inventory of systems is good, but a clear, real-time Software Bill of Materials (SBOM) for applications is non-negotiable.

In this world of manifest based infrastructure and container based applications with (real) "devsecops", the dream of continuous upgrades of OS/Runtime/Stack/App and App Dependencies is very mature and there are solid examples of companies and federal entities managing this at scale without thousands of teams and people.

Segment Resources:

• BLOG - Supply Chain Security: How accurate SBOMs can deliver proactive threat mitigation

Interview with Jacob Horne

CMMC Phase 1 Enforcement — What the November 10 Deadline Means for the Defense Supply Chain

With the upcoming CMMC Phase 1 enforcement on November 10, cybersecurity teams across the defense and federal supply chain are facing new compliance requirements that directly affect contract eligibility and data-protection standards. Jacob Horne, Chief Cybersecurity Evangelist at Summit 7, can break down what this milestone means for enterprise security leaders, MSPs/MSSPs, and contractors preparing for audits.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-449

Interview - Ben Worthy from Airbus Protect

The current state of OT security and business resilience

In this episode of Enterprise Security Weekly, we sit down with Ben Worthy, OT Security Specialist at Airbus Protect, to explore the evolving landscape of business resilience in safety-critical sectors. With over 25 years of experience across aerospace, nuclear, water, oil & gas, and other industries, Ben shares insights on how organizations are adapting to the surge in disruptive cyberattacks—from ransomware targeting operational technology to GPS spoofing and supply chain incidents. We discuss major cases including the Boeing/LockBit ransom demand, the Jaguar Land Rover production shutdown, and the SITA passenger data breach, examining how aviation and other critical infrastructure sectors are separating safety risk from business continuity risk.

Ben also breaks down the regulatory changes reshaping the industry, including EASA's October 2025 and February 2026 deadlines that tie cyber assurance directly to safety oversight, and what ENISA's latest numbers reveal about hacktivism and ransomware trends. Whether you're in aviation, nuclear, or any safety-critical sector, this conversation offers practical lessons on building resilience that keeps operations moving while addressing threats in real time.

This segment is sponsored by Airbus Protect. Visit https://securityweekly.com/airbusprotect to learn more about them!

Topic: Where are the business incentives to build secure products and software?

"It's the right thing to do," so of course businesses will make their products secure, right? Well, it turns out that breaches and vulnerabilities don't traditionally hurt financial performance all that much. Stocks recover, insurance covers the bulks of the losses, fines are paid, and lawsuits are settled. Most businesses can comfortably absorb the impact, so the threat of reputational harm or financial losses just aren't slowing them down.

In the case of Ivanti, where the reputational harm was extreme, the company's companies continue to get hacked as critical vulnerabilities keep getting discovered in their products.

https://www.bloomberg.com/news/features/2026-02-19/vpn-used-by-us-government-failed-to-stop-china-state-sponsored-hackers

In this topic segment, we don't aim to provide solutions to this problem, just the awareness that ethics, doing the right thing, and even signing the Secure by Design pledge don't seem to be enough to change vendor behavior when it comes to securing products.

The Weekly Enterprise Security News

Finally, in the enterprise security news,

1. RSA Innovation Sandbox hot takes
2. Did AI solve cyber?
3. fundings and acquisitions
4. a free app to warn you about smart glasses
5. deep thoughts about OpenClaw
6. replacing US tech with EU equivalents is hard
7. should you turn off dependabot?
8. accidentally taking over 7000 robot vacuums
9. the director of AI Safety at Meta loses her email somehow
10. should you go back to using a blackberry?

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-448

Segment 1 - Interview with Tim Morris

Bringing intelligence to assets

You've been through 6 CMDB projects in the last decade. None of them came close to the original goals, the CMDB was already out-of-date long before the project had any hopes of completing. Is building an asset inventory just too ambitious a project for most organizations, or is there a better way?

Tim Morris shares a different approach with us today. It might require some convincing and some courage, but it seems much more likely to succeed than any of your past CMDB efforts…

Segment Resources

• Trusted automation: Building autonomous IT with confidence

This segment is sponsored by Tanium. Visit https://securityweekly.com/tanium to learn more about them!

Segment 2 - Topic: the new White House cybersecurity strategy

In this segment, we explore some early details about the White House's new, but yet unreleased cybersecurity strategy. It appears that drafts have been shared (or leaked) to the press, so there's plenty to discuss here!

Segment 3 - News

Finally, in the enterprise security news,

1. Massive amounts of funding and acquisitions as we get close to RSA
2. Open source registries need help
3. Microsoft Copilot reads email marked as DO NOT READ
4. Don't use an LLM to generate passwords
5. is prompt injection a vulnerability
6. defining risks
7. AI changes the build versus buy equation
8. the scammer's perspective

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-447

Segment 1: Interview with Mathias Katz

What if you had enterprise-grade network security protections traveling with your users' laptops? What if it could be built into the laptop, but still stay safe even if the laptop OS and firmware were entirely compromised?

Mathias and his company, Byos have built such a thing, and BOY do we have some questions for him.

Segment 2: Interview with Wolfgang Goerlich

Addressing the nuanced, nefarious threats of AI

Sure, we need to worry about AI prompt injection and AI data leakage, but what about the threats to our BRAINS? Seriously, as we start to have daily conversations with this technology, how are they going to shape how we think? What inherent biases in the training, fine tuning, guardrails, or lack of guardrails are going to affect our decisions or how we work?

Wolfgang is concerned about this, so he performed a human/AI experiment. With almost 1000 people partaking in the experiment, the results are sure to be intriguing.

Segment 3: This week's enterprise security news

Finally, in the enterprise security news,

1. survey results on how folks are feeling about openclaw
2. some hidden drama discovered in KEV updates
3. some new KEV tools
4. is AI replacing traditional code scanning tools?
5. remote code execution in notepad
6. no, not notepad++, NOTEPAD.EXE
7. you know, the one that ships preinstalled on Windows
8. the RSAC innovation sandbox finalists
9. dealing with legacy vulnerabilities
10. Don't accept OpenClaw Mac Minis from strangers!

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-446

Interview Segment - Rob Allen - Clickfix

"Clickfix" attacks aren't new, but they're certainly more common these days. Rob Allen joins us to help us understand what they are, why they work on your employees, and how to stop them! We tie it into infostealers and ransomware actors. Plenty of practical recommendations for how to spot and prevent these attacks in your environment, don't miss it!

This segment is sponsored by ThreatLocker. Visit https://securityweekly.com/threatlocker to learn more about them!

Interview Segment - Rob Allen - Zero Trust World

Threatlocker's 6th annual Zero Trust World event is happening next month! This three day event runs from March 4th through the 6th once again in sunny Orlando, Florida.

This year's event is packed with hands-on hacking workshops, competitions, prizes, and keynotes from Marcus Hutchins, and Linus and Luke from Linus Tech Tips. Security Weekly will be there as well, doing live interviews and recording an episode of ESW live!

This segment is sponsored by ThreatLocker's annual Zero Trust World. Visit https://securityweekly.com/ztw to learn more about the conference and register with discount code ZTW26ESW!

News Segment

For this week's enterprise news, we discuss

1. OpenClaw!
2. funding!
3. acquisitions!
4. testing out AI models' offensive security capabilities
5. more openclaw!
6. the need for more transparency and testing in the vendor space
7. A photobooth service leaks drunken pictures of wedding parties
8. The salty snack that helps server uptime

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-445

Segment 1: Interview with Warwick Webb

From Initial Entry to Resilience: Understanding Modern Attack Flows

Modern cyberattacks don't unfold as isolated alerts--they move as coordinated attack flows that exploit gaps between tools, teams, and time. In this episode, Warwick Webb, Vice President of Managed Detection and Response at SentinelOne, breaks down how today's breaches often begin invisibly, progress undetected through siloed security stacks, and accelerate faster than human response alone can handle. He'll discuss how unified platforms, machine-speed detection powered by global threat intelligence, and expert-led response change the equation--turning fragmented signals into clear attack narratives. The conversation concludes with how organizations can move beyond incident response to build resilience, readiness, and continuous improvement through post-attack analysis. Listeners will leave with a clearer understanding of how attacks actually unfold in the real world—and what it takes to move from reactive alert handling to true attack-flow-driven defense.

Segment Resources:

• Wayfinder MDR Solution Brief
• 451 MDR Report
• Managed Defense Redefined Blog

This segment is sponsored by SentinelOne. Visit https://securityweekly.com/sentinelone to learn more about them!

Segments 2 and 3: The Weekly News

In this week's enterprise security news,

1. we've got funding
2. free tools!
3. the CISO's craft
4. agentic browsers
5. tech companies are building cyber units?
6. giving AI agents access to your entire life
7. lots of dumpster fires in the industry today
8. Cisco killed Kenna
9. the state of AI in the SOC
10. homemade EMP guns! don't try this at home

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-444

Segment 1: Interview with Thyaga Vasudevan

Hybrid by Design: Zero Trust, AI, and the Future of Data Control

AI is reshaping how work gets done, accelerating decision-making and introducing new ways for data to be created, accessed, and shared. As a result, organizations must evolve Zero Trust beyond an access-only model into an inline data governance approach that continuously protects sensitive information wherever it moves. Securing access alone is no longer enough in an AI-driven world.

In this episode, we'll unpack why real-time visibility and control over data usage are now essential for safe AI adoption, accurate outcomes, and regulatory compliance. From preventing data leakage to governing how data is used by AI systems, security teams need controls that operate in the moment - across cloud, browser, SaaS, and on-prem environments - without slowing the business.

We'll also explore how growing data sovereignty and regulatory pressures are driving renewed interest in hybrid architectures. By combining cloud agility with local control, organizations can keep sensitive data protected, governed, and compliant, regardless of where it resides or how AI is applied.

This segment is sponsored by Skyhigh Security. Visit https://securityweekly.com/skyhighsecurity to learn more about them!

Segment 2: Why detection fails

Caleb Sima put together a nice roundup of the issues around detection engineering struggles that I thought worth discussing. Amélie Koran also shared some interesting thoughts and experiences.

Segment 3: Weekly Enterprise News

Finally, in the enterprise security news,

1. Fundings and acquisitions are going strong
2. can cyber insurance be profitable?
3. some new free tools shared by the community
4. RSAC gets a new CEO
5. Large-scale enterprise AI initiatives aren't going well
6. LLM impacts on exploit development
7. AI vulnerabilities
8. global risk reports
9. floppies are still used daily, but not for long?

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-443

Segment 1 with Beck Norris - Making vulnerability management actually work

Vulnerability management is often treated as a tooling or patching problem, yet many organizations struggle to reduce real cyber risk despite heavy investment. In this episode, Beck Norris explains why effective vulnerability management starts with governance and risk context, depends on multiple interconnected security disciplines, and ultimately succeeds or fails based on accountability, metrics, and operational maturity.

Drawing from the aviation industry—one of the most regulated and safety-critical environments—Beck translates lessons that apply broadly across regulated and large-scale enterprises, including healthcare, financial services, and critical infrastructure.

Segment 2 with Ryan Fried and Jose Toledo - Making incident response actually work

Organizations statistically have decent to excellent spending on cybersecurity: they have what should be sufficient staff and some good tools. When they get hit with an attack, however, the response is often an unorganized, poorly communicated mess! What's going on here, why does this happen???

Not to worry. Ryan and José join us in this segment to offer some insight into why this happens and how to ensure it never happens again!

Segment Resources:

• [Mandiant - Best practices for incident response planning]

(https://services.google.com/fh/files/misc/mandiantincidentresponsebestpractices_2025.pdf?linkId=19287933)

• Beyond Cyberattacks: Evolution of Incident Response in 2026

Segment 3 - Weekly Enterprise News

Finally, in the enterprise security news,

1. Almost no funding…
2. Oops, all acquisitions!
3. Changes in how the US handles financial crimes and international hacking
4. Mass scans looking for exposed LLMs
5. The state of Prompt injection
6. be careful with Chrome extensions
7. and home electronics from unknown brands
8. Is China done with the West?

All that and more, on this episode of Enterprise Security Weekly.

Visit https://www.securityweekly.com/esw for all the latest episodes!

Show Notes: https://securityweekly.com/esw-442