Keith S. Crawford

Thoughts on security, AI systems, and engineering.

I'm Keith Crawford — cybersecurity leader, systems thinker, and builder. I write about security governance, AI in practice, and making complex things clearer.


Shorts

Here's a test worth applying to any prompt, skill, or agent harness you've built: when the next model generation lands, does this scaffolding make the system better, or does it… Read more →

Claude Code v2.1.105 raised the skill description cap from around 250 characters to 1,536 — roughly a 6x jump. The old ceiling forced every skill into a compressed one-liner… Read more →

Cloudflare collapsed their 2,500-endpoint API into two meta-tools — search() and execute() — and ran them inside a sandboxed isolate. Their claim: 1.17M tokens of tool… Read more →

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