diff --git a/CLAUDE.md b/CLAUDE.md
index 074b6122..ae68d806 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -139,10 +139,16 @@ SKILL.md files are **generated** from `.tmpl` templates. To update docs:
 To add a new browse command: add it to `browse/src/commands.ts` and rebuild.
 To add a snapshot flag: add it to `SNAPSHOT_FLAGS` in `browse/src/snapshot.ts` and rebuild.
 
-**Token ceiling:** Generated SKILL.md files must stay under 100KB (~25K tokens).
-`gen-skill-docs` warns if any file exceeds this. If a skill template grows past the
-ceiling, consider extracting optional sections into separate resolvers that only
-inject when relevant, or making verbose evaluation rubrics more concise.
+**Token ceiling:** Generated SKILL.md files trip a warning above 160KB (~40K tokens).
+This is a "watch for feature bloat" guardrail, not a hard gate. Modern flagship
+models have 200K-1M context windows, so 40K is 4-20% of window, and prompt caching
+makes the marginal cost of larger skills small. The ceiling exists to catch runaway
+preamble/resolver growth, not to force compression on carefully-tuned big skills
+(`ship`, `plan-ceo-review`, `office-hours` legitimately pack 25-35K tokens of
+behavior). If you blow past 40K, the right fix is usually: (1) look at WHAT grew,
+(2) if one resolver added 10K+ in a single PR, question whether it belongs inline
+or as a reference doc, (3) only compress carefully-tuned prose as a last resort —
+cuts to the coverage audit, review army, or voice directive have real quality cost.
 
 **Merge conflicts on SKILL.md files:** NEVER resolve conflicts on generated SKILL.md
 files by accepting either side. Instead: (1) resolve conflicts on the `.tmpl` templates
diff --git a/scripts/gen-skill-docs.ts b/scripts/gen-skill-docs.ts
index dd709ee9..40f08369 100644
--- a/scripts/gen-skill-docs.ts
+++ b/scripts/gen-skill-docs.ts
@@ -534,10 +534,16 @@ for (const currentHost of hostsToRun) {
       const tokens = Math.round(content.length / 4); // ~4 chars per token
       tokenBudget.push({ skill: relOutput, lines, tokens });
 
-      // Token ceiling check: warn if any generated SKILL.md exceeds ~25K tokens (100KB)
-      const TOKEN_CEILING_BYTES = 100_000;
+      // Token ceiling check: warn if any generated SKILL.md exceeds ~40K tokens (160KB).
+      // The ceiling is a "watch for feature bloat" guardrail, not a hard gate. Modern
+      // flagship models have 200K-1M context windows, so 40K (4-20% of window) is fine.
+      // Prompt caching further reduces the marginal cost of larger skills. This ceiling
+      // exists to catch a runaway preamble or resolver that's grown by 10K+ tokens in
+      // a release, not to force compression on carefully-tuned big skills (ship,
+      // plan-ceo-review, office-hours all legitimately pack 25-35K tokens of behavior).
+      const TOKEN_CEILING_BYTES = 160_000;
       if (content.length > TOKEN_CEILING_BYTES) {
-        console.warn(`⚠️  TOKEN CEILING: ${relOutput} is ${content.length} bytes (~${tokens} tokens), exceeds ${TOKEN_CEILING_BYTES} byte ceiling (~25K tokens)`);
+        console.warn(`⚠️  TOKEN CEILING: ${relOutput} is ${content.length} bytes (~${tokens} tokens), exceeds ${TOKEN_CEILING_BYTES} byte ceiling (~40K tokens)`);
       }
     }