Fixing pentesting, Meta is destroying its engineering org, the weekly news - Adriel Desautels - ESW #465

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,

• an AI vibe check
• An AI SOC vendor shuts down
• Cybersecurity vendor layoffs
• funding & acquisitions
• cascading breaches
• digital estate management
• criminals don't trust AI either
• some devs won't code without AI, even if you pay them to
• Midjourney is now a healthcare company?
All that and more, on this episode of Enterprise Security Weekly.
Show Notes: https://securityweekly.com/esw-465