Screaming in the Cloud Avery Pennarun on Tailscale's Evolution: From Mesh VPN to AI Security Gateway
6 snips
Jan 8, 2026 
Avery Pennarun, co-founder and CEO of Tailscale, is a veteran software engineer revolutionizing secure networking. He shares how Tailscale transforms VPNs into user-friendly tools and tackles AI security with zero-click authentication. Avery discusses the chaos of running multiple tailnets and the challenges of scaling during rapid growth. He introduces TSIDP for effortless OAuth and talks about bridging the gap between personal and corporate networks. Expect insights sprinkled with humor on making security both powerful and approachable.
AI Snips
Chapters
Transcript
Episode notes
Keep ACLs In GitOps With Round-Trip Edits
- Use GitOps and the ACL editor together: round-trip JSON edits between GUI and repo for reproducible policies.
- Keep comments in policy JSON and push changes from GUI to your Git workflow for safe edits.
Apple TV As A Reliable Exit Node
- Corey uses an Apple TV as an exit node to appear on his home network while traveling.
- Avery prefers Apple TV over Raspberry Pi for reliability and easy remote setup with non-technical family.
A Modern Layer Three For Devices
- Tailscale provides a new layer three that gives devices stable, location-independent addresses.
- This restores addressability and persistent connectivity across networks and device moves.