Jun 29, 2026

Interview with Adriel Desautels - the pentest is broken

Adriel joins us for a discussion on the state of penetration testing, why it hasn't done much to help security teams over the last 20 years, and why AI won't save it.

Segment Resources:

• https://hbr.org/2026/04/boards-are-falling-short-on-cybersecurity
• https://www.scworld.com/perspective/how-to-build-a-breach-ready-security-posture-without-the-enterprise-price-tag
• https://netragard.com/blog/what-is-penetration-testing/

Topic: Why Meta is destroying its engineering organization

The titular essay: https://newsletter.pragmaticengineer.com/p/why-is-meta-destroying-its-engineering

A very interesting analysis of what's going on inside big tech companies as they try to dogfood their own AI hype and tokenmaxx themselves into oblivion. There have been a LOT of stories on this, but this is the most comprehensive and enlightening. A few more are linked below.

This is relevant to security, because heavier AI use appears to be linked to a much higher occurrence of availability and security issues.

• ‘Tell Him He’s a Piece of Shit’: Meta’s New AI Unit Is a Total Mess
• The Newest Instagram "Exploit" is the Goofiest I've Seen
• Meta CTO Andrew Bosworth Admits the Company’s AI Reorg Was ‘Atrocious’
• Meta’s months-old AI unit is a soul-crushing gulag, say the engineers stuck inside it

The Weekly Enterprise News

Finally, in the enterprise security news,

1. an AI vibe check
2. An AI SOC vendor shuts down
3. Cybersecurity vendor layoffs
4. funding & acquisitions
5. cascading breaches
6. digital estate management
7. criminals don’t trust AI either
8. some devs won’t code without AI, even if you pay them to
9. Midjourney is now a healthcare company?

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-465