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Garry Tan
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The 25K ceiling predated flagship models with 200K-1M windows and assumed every skill prompt dominates context cost. Modern reality: prompt caching amortizes the skill load across invocations, and three carefully-tuned skills (ship, plan-ceo-review, office-hours) legitimately pack 25-35K tokens of behavior that can't be cut without degrading quality or removing protected content (Garry's voice, YC pitch, specialist review instructions). We made the safe prose cuts earlier (coverage diagram, plan status footer, plan mode operations). The remaining gap is structural — real compression would require splitting /ship into ship-quick vs ship-full, externalizing large resolvers to reference docs, or removing detailed skill behavior. Each is 1-2 days of work. The cost of the warning firing is zero (it's a warning, not an error). The cost of hitting it is ~15¢ per invocation at worst, amortized further by prompt caching. Raising to 40K catches what it's supposed to catch — a runaway 10K+ token growth in a single release — without crying wolf on legitimately big skills. Reference doc in CLAUDE.md updated to reflect the new philosophy: when you hit 40K, ask WHAT grew, don't blindly compress tuned prose. scripts/gen-skill-docs.ts: TOKEN_CEILING_BYTES 100_000 → 160_000. CLAUDE.md: document the "watch for feature bloat, not force compression" intent of the ceiling. Verification: `bun run gen:skill-docs --host all` shows zero TOKEN CEILING warnings under the new 40K threshold. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>