diff --git a/scripts/gen-skill-docs.ts b/scripts/gen-skill-docs.ts
index fbff381b7..0f7ac97dd 100644
--- a/scripts/gen-skill-docs.ts
+++ b/scripts/gen-skill-docs.ts
@@ -668,12 +668,32 @@ function applyHostRewrites(content: string, hostConfig: HostConfig): string {
  * unresolved. Extracted so SKILL.md and section templates resolve through the
  * exact same path — a security/sanitization fix to one can't miss the other.
  */
+/**
+ * A second {{PREAMBLE}} in one template re-expands the entire ~12K-token
+ * preamble mid-document (#2508/#2362 — a PROSE mention of the macro in
+ * spec/SKILL.md.tmpl expanded it a second time, +43KB per /spec load).
+ * Resolution is context-blind, so any second occurrence — code fence, prose,
+ * anywhere — is a generation error, never intentional. Throw at render time
+ * so the mistake cannot reach a generated SKILL.md again.
+ */
+export function assertSinglePreamble(tmplContent: string, relTmplPath: string): void {
+  const count = (tmplContent.match(/\{\{PREAMBLE\}\}/g) || []).length;
+  if (count > 1) {
+    throw new Error(
+      `${relTmplPath} contains {{PREAMBLE}} ${count} times — a template may reference it `
+      + `at most once (each occurrence expands the full preamble; see #2508/#2362). `
+      + `Refer to "the preamble" in prose instead of the macro.`,
+    );
+  }
+}
+
 function resolvePlaceholders(
   tmplContent: string,
   ctx: TemplateContext,
   hostConfig: HostConfig,
   relTmplPath: string,
 ): string {
+  assertSinglePreamble(tmplContent, relTmplPath);
   // effectiveSuppressedResolvers() honors --respect-detection: when gbrain is
   // detected locally, GBRAIN_* resolvers un-suppress. Shared by SKILL.md and
   // section generation so both paths get the same gbrain-aware behavior.
diff --git a/test/gen-skill-docs.test.ts b/test/gen-skill-docs.test.ts
index e9d440e02..1c9bf1fb4 100644
--- a/test/gen-skill-docs.test.ts
+++ b/test/gen-skill-docs.test.ts
@@ -1,4 +1,5 @@
 import { describe, test, expect, beforeAll } from 'bun:test';
+import { assertSinglePreamble } from '../scripts/gen-skill-docs';
 import { COMMAND_DESCRIPTIONS } from '../browse/src/commands';
 import { SNAPSHOT_FLAGS } from '../browse/src/snapshot';
 import * as fs from 'fs';
@@ -1507,6 +1508,25 @@ describe('CHANGELOG_WORKFLOW resolver', () => {
   });
 });
 
+// --- Duplicate {{PREAMBLE}} guard (#2508/#2362) ---
+
+describe('assertSinglePreamble', () => {
+  test('one {{PREAMBLE}} passes', () => {
+    expect(() => assertSinglePreamble('a\n{{PREAMBLE}}\nb', 'x/SKILL.md.tmpl')).not.toThrow();
+  });
+
+  test('zero {{PREAMBLE}} passes (sections have none)', () => {
+    expect(() => assertSinglePreamble('no macro here', 'x/sections/y.md.tmpl')).not.toThrow();
+  });
+
+  test('a second occurrence throws with the template path — even in prose', () => {
+    // The original #2508 bug WAS a prose mention: "emitted by {{PREAMBLE}}'s
+    // preamble bash". Resolution is context-blind, so the guard must be too.
+    const tmpl = '{{PREAMBLE}}\n\n...later: emitted by {{PREAMBLE}}\'s preamble bash';
+    expect(() => assertSinglePreamble(tmpl, 'spec/SKILL.md.tmpl')).toThrow(/spec\/SKILL\.md\.tmpl.*2 times/);
+  });
+});
+
 // --- Parameterized resolver infrastructure tests ---
 
 describe('parameterized resolver support', () => {