In this episode, we break down a major Cloudflare outage, explore how a nation-state used AI agents to automate a cyberattack, and discuss the growing risks around MCP integrations. We also highlight why GRC Engineering is becoming essential to modern security programs and wrap up with key regulatory updates, including CMMC changes affecting thousands of contractors.

Topics covered:
• Cloudflare outage impact and root cause
• Nation-state attack using AI agents to automate intrusion steps
• MCP (Model Context Protocol): power, risks, and examples
• Why GRC Engineering is the future of compliance and automation
• Updates on GDPR, ISO 27701, California AB 5866, and SEC rules
• CMMC assessor shortages and what organizations must prepare for

Spirit of the Episode
• Knob Creek 21-Year Limited Release – rich caramel notes, heavy char, smooth for 100 proof

Timestamps

• 0:02- Cloudflare Outage Stories & Global Impact
• 3:07- Root Cause, Not a Cyberattack & Third-Party Risk Reality
• 10:38 - China Uses Anthropic’s Claude + MCP for Automated Cyberattacks
• 14:17 - Full AI Attack Lifecycle Explained
• 27:18 - MCP: The API for AI & Its Security Risks
• 44:05 - Bourbon Break: Knob Creek 21-Year Review
• 50:02 - GRC Engineering Deep Dive: Automation & Controls-as-Code
• 1:24:13 - Regulatory Roundup: GDPR, ISO 27701, California AB 566, SEC SP
• 1:44:27 - CMMC 2.0 Crisis: Auditor Shortages & DoD Contract Impact
• 2:11:20 - Closing Thoughts & Episode Wrap-Up

Hosts

• Justin Leapline – @justinleapline
• Joe Wynn – @wynnjoe
• Rick Yocum – @rickyocum

Connect with Us

• Website: distilledsecuritypodcast.com
• X: @DisSecPod
• Email: hello@distilledsecuritypodcast.com

In Episode 18 of the Distilled Security Podcast, Justin Leapline, Joe Wynn, and Rick Yokum recap their time at TRISS, share lessons on storytelling and women in tech, and break down the recent AWS us-east-1 DNS/DynamoDB outage, the Microsoft Front Door global disruption, and the F5 BIG-IP incident.

🔍 We discuss:
- TRISS highlights: panels, community & storytelling
- “Breaking the glass ceiling” and unintentional bias in meetings
- AWS & Microsoft outages: risk, resilience & when multicloud matters
- F5 BIG-IP incident and supply chain risk
- Launching a GRC SaaS: episki’s journey, lessons & tradeoffs

🥃 Spirit of the episode
Penelope Bourbon – Project X (sherry cask finish)

⏱️ Timestamps
00:00 – 🥃 Intro & TRISS Recap — Highlights from TRISS: panels, community, and a keynote with Edward Norton

02:40 – 📖 The Power of Storytelling — Why empathy and narrative matter in cybersecurity leadership

04:40 – 👩‍💻 Women in Tech & Bias in Meetings — Real talk about unintentional bias and everyday experiences

20:34 – ☁️ AWS & Microsoft Outages — What happened and what it says about cloud resilience

49:38 - 🥃 Bourbon Break — Enjoying a glass of Penelope Project X

53:30 – 🔥 F5 BIG-IP Vulnerability — Supply chain risk and patching lessons

1:09:50 – 🚀 Launching episki (GRC SaaS) — Building simply, shipping fast, and learning from users

1:52:22 – 🧭 Reflections & Closing Thoughts — Culture, resilience, and what’s next

🎧 Hosts
Justin Leapline
Joe Wynn
Rick Yocum

🌐 Connect with Us
Website: distilledsecuritypodcast.com
X : @DisSecPod
Email: hello@distilledsecuritypodcast.com

🎙️ Welcome back to the Distilled Security Podcast - Episode 17!

In this episode, Justin, Joe, and Rick break down several major cybersecurity and compliance updates shaping the landscape this fall. From regulatory deadlines to the futility of checkbox TPRM exercises, the crew dives deep into what actually matters for security leaders and business owners navigating today’s risk environment.

Also, join us at TRISS in Pittsburgh, PA, at the David this October 29,2025! We have our own booth and will be doing something fun there. Also, we are sponsoring the After Party! Please come say hi!

🔹 Topics Covered

NY DFS Part 500: Final Requirements Take Effect November 1

The hosts unpack the final phase of New York’s cybersecurity regulation, what’s changing, and what companies must have in place before the enforcement deadline.

Negotiating Security

How smaller companies can push back or reframe due diligence requirements—substituting a SOC 2 or ISO 27001 certification with custom questionnaires, summaries, or shared evidence that reflect real security maturity instead of checklists.

“TPRM Is Worthless”

A candid discussion on the state of third-party risk management: why it’s often broken, what needs to change, and how to make it meaningful rather than bureaucratic.

Department of War Announces New Cybersecurity Risk Management Construct

The team explores the DoD’s latest cybersecurity framework announcement—what it means for contractors, how it overlaps with CMMC and NIST 800-171, and whether it will actually simplify or complicate compliance.

🥃 Spirit Review

One of Us Mezcal — This small-batch mezcal impresses with its earthy smoke, hints of citrus, and smooth finish. The guys compare it to other craft agave spirits they’ve tried and debate whether it pairs better with a quiet evening or post-recording celebration.

Find it here:

https://oneofusmezcal.com/products/cuishe-mezcal-the-wild-one

⏱️ Timestamps

0:00 – Introduction & Travel Mishap

6:25 – New Laptop Twins & Backup Strategies

11:35 – NY DFS Part 500 Updates

27:30 – DFS Reporting & Organizational Accountability

33:30 – Negotiating Security Requirements

47:46 – Cultural Nuances in Negotiation

50:20 – Spirit Review: One of Us Mezcal

52:55 – TPRM Is Worthless?

57:50 – Fixing Broken Vendor Risk Workflows

1:08:21 – Vendor Resilience vs. Security

1:18:20 – New DoW/DoD Cybersecurity Risk Management Construct

1:35:06 - BSides Pittsburgh Planning & Sponsorship

1:38:35 - DSP at TRISS

1:39:51 – Closing Remarks & Outro

🎧 Hosts

Justin Leapline – @justinleapline

Joe Wynn – @wynnjoe

Rick Yocum – @rickyocum

🌐 Connect with Us

Website: distilledsecuritypodcast.com

🐦 Twitter: @DisSecPod

📧 Email: hello@distilledsecuritypodcast.com