Podcast Summary: To The Point Cybersecurity

Episode: Cybersecurity in 2026: AI, Steganography, and Securing Legacy Systems with Jacob Anderson
Date: February 17, 2026
Host(s): Rachael Lyon, Jonathan Knepher
Guest: Jacob Anderson (Founder, Beyond Ordinary Software Solutions)

Episode Overview

This episode explores the intersection of emerging technology and cybersecurity, focusing on how AI is enabling new steganography techniques, the ongoing challenges of securing legacy systems, and the evolving tactics in threat detection and defense. Guest Jacob Anderson brings over three decades of experience in software development, working across finance, defense, and insurance, and offers insights into both current realities and the road ahead.

Key Discussion Points & Insights

1. Modern Steganography and Covert Channels in 2026

• What’s Changed?

  • Steganography, once limited to rudimentary data hiding like images, is now supercharged by AI: “AI has come along and you have access...to a very sophisticated tool that can tell you how to do extremely sophisticated steganography techniques.” – Jacob Anderson (01:49)
  • Data can now be hidden across varied media including images, audio streams, word documents, and even live deepfake video.

• AI as a Double-Edged Sword

  • AI democratizes advanced attack methods: “The more sophisticated actors have realized that these tools can help them...do even better techniques of data hiding.” (03:43)
  • Increased complexity of hiding can lower data rates and functionality—a tradeoff between being covert and being practical.

• Emergence of Streaming Media Threats

  • “Anything that’s streaming now, like...deepfake streaming...are perfect for this, right? Because I can create this deep fake audio and deep fake video and inside of there I can encode all kinds of crazy stuff.” (04:28)
  • Deepfakes serve not only as misinformation threats but also as powerful covert data exfiltration channels.

2. Everyday Impacts and AI Assistants

• Authenticity Challenges

  • “It’s crazy times that we live in. It’s trying to navigate what’s real, what’s not, and then how to avoid...stepping in it just inadvertently because you’re like, I want to be entertained for a second.” – Rachael Lyon (05:14)
  • The increasing sophistication of outreach (e.g., scam texts or AI chatbots) blurs the line between real and artificial interactions.

• The Role of AI as a Gatekeeper

  • Potential for AI assistants to help manage authenticity and trust, but these systems can themselves become threat vectors or privacy risks.

3. AI-Driven Bug Hunting and Open Source Risks

• AI in the Open Source Ecosystem

  • Use of AI to rapidly find and fix software bugs is rising: “I was looking at one of the bug tracks recently...one company’s got like 50 bugs that it fixed...that’s obviously an AI.” (11:46)
  • Dilemma: Many projects are overwhelmed by a flood of low-quality or fake bug reports generated by AIs.

• Balancing Innovation and Security

  • Popular, widely-distributed open-source tools face unique threats, requiring greater caution and responsibility from maintainers: “There is a consequence to being popular and being a celebrity sort of open source tool. You’re in everyone’s world...” (14:08)

4. Democratization of Advanced Capabilities via AI

• Raising the Baseline

  • “Every single human out there...they have a great start for something better now. Yes, right. And so they have enabled themselves to do all kinds of things, wonderful things...” (16:42)
  • AI enables rapid prototyping and personal automation but also ups the ante in arms race between defenders and attackers.

• Trust and Expertise in the Age of AI

  • “We used to rely on experts, right? And now you don’t need that. You’ve got a pocket expert. Right? But do you really have a pocket expert?” (16:42)

5. Cryptanalysis: Defense & Offense

• Breaking Ciphers

  • “Crypto analysis is a lot easier now because you’ve got these tools that will help you with it, right? So AI tools can help you understand what to do.” (20:07)
  • Fundamentals of cryptanalysis have not changed, but manual skills are increasingly augmented by algorithmic tools.

• Defensive and Offensive Perspectives

  • Defensive cryptanalysis is about ensuring reliability and trust: “It’s a measure of reliability. What’s the assurance that I’m sending data out that...Joe Blow is not going to...intercept it and decrypt it?” (22:50)
  • Offensively, attackers can exploit weak key exchanges and outdated encryption standards (e.g., DES), often still in use due to hardware compatibility and inertia.

6. Securing Legacy Systems

• Risks of Outdated Infrastructure

  • Legacy systems, particularly in insurance, aviation, and some Fortune 500s, may provide reliable uptime but poor security: “The security on it, I don’t know. Because you never really update it...it requires so much time.” (26:54)
  • These systems often run critical functions but are hard to patch, creating tempting targets for sophisticated attackers.

• Best Practices for Legacy Security

  • Employ “big old perimeters,” strict segmentation, firewalls, and proxies.
  • Regular staff training, monitoring, and leveraging AI for tabletop security exercises.
  • “Put in the firewalls...using the software available today for monitoring stuff. There’s a lot of it out there now...” (29:54)
  • Emphasize strong operational discipline over technical modernization when upgrades are impractical.

7. Industry Trends and Getting Ahead

• Sectors Most At Risk

  • Insurance and airlines are most reliant on legacy infrastructure. Banking has largely modernized.

• Forward-Looking Advice

  • “Get your staff...trained up, expose them to these tools, you know, so they use them regularly. And then you gotta use AI constantly...” (29:54)

Notable Quotes & Memorable Moments

• On Deepfake Steganography
  • “In the audio side of this bot that’s talking, I can embed all kinds of data...streaming, you know, military plans, but you won’t even know it...it’s pretty amazing what you can do right now.” – Jacob Anderson (08:37)
• On Detecting Data Hiding:
  • “There are telltale ways of knowing...that’s supposed to be noise, and it’s no longer following that noise Gaussian profile, like, that’s obviously someone’s putting something in there.” (09:00)
• On Legacy Systems:
  • “It’s bulletproof to everything, but an upgrade.” – Jonathan Knepher (26:54)
• On the Future of AI and Roles:
  • “I don’t know that anybody really needs a commercial software developer anymore. We got AI.” – Jacob Anderson (36:23)
• On Personal Cybersecurity Beginnings:
  • “I used to crack software because I grew up poor so I couldn’t buy anything. So I used to just crack stuff, take off the copy protection stuff...” – Jacob Anderson (31:58)

Timestamps for Important Segments

• Steganography & AI’s Role – 01:49–05:14
• Deepfake and Streaming Threats – 04:28–07:07
• Open Source & AI Bug Hunt Challenges – 11:46–14:08
• AI as a Double-Edged Sword for Innovation – 16:42–19:41
• Cryptanalysis Explained (Defense & Offense) – 20:07–25:33
• Legacy Systems & Industry Examples – 25:53–29:31
• Security Best Practices for Legacy & Modern Threats – 29:54–31:29
• Jacob Anderson’s Cybersecurity Origin Story – 31:58–34:55
• Future Plans & Industry Predictions – 35:31–36:23

Actionable Takeaways

• Modernize perimeters and use layered defenses around legacy systems.
• Regularly train and expose staff to new tools and AI-driven tabletop exercises.
• Treat AI as both a productivity tool and a constantly-evolving threat vector—test your defenses by simulating attacks with and against AI.
• Be cautious of AI-generated bug reports and control the integrity of open source contributions.
• Recognize that legacy crypto hardware is rarely patched and thus particularly vulnerable—segment and closely monitor.

Conclusion

Jacob Anderson’s wide-ranging expertise highlights a cybersecurity landscape where the boundary between defender and attacker is increasingly blurred by rapid advances in AI and automation. The challenge for organizations is not just adopting powerful new solutions, but building durable processes, responsible controls, and a culture ready for threats both old and new.

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