diff --git a/apps/server/src/core/ai-chat/tools/docmost-client.loader.spec.ts b/apps/server/src/core/ai-chat/tools/docmost-client.loader.spec.ts
index 5ca7bbfa..973dec3d 100644
--- a/apps/server/src/core/ai-chat/tools/docmost-client.loader.spec.ts
+++ b/apps/server/src/core/ai-chat/tools/docmost-client.loader.spec.ts
@@ -1,7 +1,15 @@
 import { createHash } from 'node:crypto';
-import { mkdtempSync, mkdirSync, writeFileSync, rmSync } from 'node:fs';
+import {
+  mkdtempSync,
+  mkdirSync,
+  writeFileSync,
+  rmSync,
+  readdirSync,
+  statSync,
+  readFileSync,
+} from 'node:fs';
 import { tmpdir } from 'node:os';
-import { join } from 'node:path';
+import { dirname, join, relative, sep } from 'node:path';
 
 import { computeSrcRegistryStamp } from './docmost-client.loader';
 
@@ -30,10 +38,14 @@ function assertStaleGuard(
   }
 }
 
-// Build a throwaway `<pkg>/build/index.js` + optional `<pkg>/src/tool-specs.ts`
-// layout so `computeSrcRegistryStamp(<pkg>/build/index.js)` resolves src the same
-// way the loader does (dirname(dirname(entry))/src/tool-specs.ts).
-function makeFakePackage(toolSpecsSource: string | null): {
+// Build a throwaway `<pkg>/build/index.js` + optional `<pkg>/src/` tree so
+// `computeSrcRegistryStamp(<pkg>/build/index.js)` resolves src the same way the
+// loader does (dirname(dirname(entry))/src). Since #486 the stamp hashes the WHOLE
+// src tree, so a fixture is a { relPath: content } map. A bare string is sugar for
+// a single `tool-specs.ts`; `null` means "no src tree" (the prod no-op path).
+function makeFakePackage(
+  src: string | Record<string, string> | null,
+): {
   entry: string;
   cleanup: () => void;
 } {
@@ -42,10 +54,15 @@ function makeFakePackage(toolSpecsSource: string | null): {
   mkdirSync(buildDir, { recursive: true });
   const entry = join(buildDir, 'index.js');
   writeFileSync(entry, '// fake @docmost/mcp build entry\n', 'utf8');
-  if (toolSpecsSource !== null) {
+  if (src !== null) {
+    const files =
+      typeof src === 'string' ? { 'tool-specs.ts': src } : src;
     const srcDir = join(root, 'src');
-    mkdirSync(srcDir, { recursive: true });
-    writeFileSync(join(srcDir, 'tool-specs.ts'), toolSpecsSource, 'utf8');
+    for (const [rel, content] of Object.entries(files)) {
+      const full = join(srcDir, rel);
+      mkdirSync(dirname(full), { recursive: true });
+      writeFileSync(full, content, 'utf8');
+    }
   }
   return { entry, cleanup: () => rmSync(root, { recursive: true, force: true }) };
 }
@@ -93,34 +110,109 @@ describe('computeSrcRegistryStamp (#447 stale-build guard)', () => {
     }
   });
 
-  // CROSS-IMPL EQUALITY (covers reviewer suggestion 2). The SAME fixed input and
+  // #486 CORE (negative): an edit to a NON-tool-specs src file (client.ts) with a
+  // rebuild NOT run must move the src stamp away from the built REGISTRY_STAMP, so
+  // the loader's stale-check refuses. Under the old tool-specs.ts-only hash this
+  // edit was invisible and a stale build/ served the old client.ts silently.
+  it('a client.ts edit (no rebuild) moves the src stamp -> loader refuses (#486)', () => {
+    // "Built" state: the package as it was compiled.
+    const built = makeFakePackage({
+      'tool-specs.ts': 'export const SPECS = 1;\n',
+      'client.ts': "export const impl = 'v1';\n",
+    });
+    // "Dev edited src, forgot to rebuild": client.ts changed, tool-specs.ts not.
+    const edited = makeFakePackage({
+      'tool-specs.ts': 'export const SPECS = 1;\n',
+      'client.ts': "export const impl = 'v2';\n",
+    });
+    try {
+      const builtStamp = computeSrcRegistryStamp(built.entry);
+      const editedStamp = computeSrcRegistryStamp(edited.entry);
+      expect(builtStamp).not.toBeNull();
+      expect(editedStamp).not.toBe(builtStamp);
+      // build/ still carries builtStamp; src now hashes to editedStamp -> refuse.
+      expect(() => assertStaleGuard(editedStamp, builtStamp as string)).toThrow(
+        STALE_BUILD_MESSAGE,
+      );
+    } finally {
+      built.cleanup();
+      edited.cleanup();
+    }
+  });
+
+  // *.generated.ts is excluded (the codegen's own output — a fixed-point cycle
+  // otherwise): its presence/content must not move the stamp.
+  it('excludes *.generated.ts from the stamp', () => {
+    const without = makeFakePackage({ 'tool-specs.ts': 'x\n' });
+    const withGen = makeFakePackage({
+      'tool-specs.ts': 'x\n',
+      'registry-stamp.generated.ts': 'export const REGISTRY_STAMP = "abc";\n',
+    });
+    try {
+      expect(computeSrcRegistryStamp(withGen.entry)).toBe(
+        computeSrcRegistryStamp(without.entry),
+      );
+    } finally {
+      without.cleanup();
+      withGen.cleanup();
+    }
+  });
+
+  // CROSS-IMPL EQUALITY (covers reviewer suggestion 2). The SAME fixed tree and
   // EXPECTED hash are asserted in the mcp-side node test
   // (packages/mcp/test/unit/registry-stamp.test.mjs) against the codegen's
   // `computeRegistryStamp`. Asserting the SAME pair here against the loader's
-  // `computeSrcRegistryStamp` proves both implementations normalize+hash
+  // `computeSrcRegistryStamp` proves both implementations enumerate+normalize+hash
   // identically; a divergence in EITHER side reddens one of the two tests.
-  it('matches the documented cross-impl hash for a fixed input', () => {
-    const FIXED_INPUT = 'line1\r\nline2\n';
-    const EXPECTED =
-      '683376e290829b482c2655745caffa7a1dccfa10afaa62dac2b42dd6c68d0f83';
-    const { entry, cleanup } = makeFakePackage(FIXED_INPUT);
+  const CROSS_IMPL_TREE = {
+    'tool-specs.ts': 'line1\r\nline2\n',
+    'client/read.ts': 'export const R = 1;\n',
+    'registry-stamp.generated.ts': 'export const REGISTRY_STAMP="ignored";\n',
+  };
+  const CROSS_IMPL_EXPECTED =
+    '131c1b9e4e2f5a7d6cef91ca8df619822b442f52bc45ebd09474a4c1d6728616';
+
+  it('matches the documented cross-impl hash for a fixed tree', () => {
+    const { entry, cleanup } = makeFakePackage(CROSS_IMPL_TREE);
     try {
-      expect(computeSrcRegistryStamp(entry)).toBe(EXPECTED);
+      expect(computeSrcRegistryStamp(entry)).toBe(CROSS_IMPL_EXPECTED);
     } finally {
       cleanup();
     }
   });
 
-  it('the documented EXPECTED is the normalize+sha256 of the fixed input', () => {
-    // Proves EXPECTED is not a magic constant but the documented computation.
-    const FIXED_INPUT = 'line1\r\nline2\n';
-    const normalized = FIXED_INPUT.replace(/\r\n/g, '\n').replace(/\n$/, '');
-    const expected = createHash('sha256')
-      .update(normalized, 'utf8')
-      .digest('hex');
-    const { entry, cleanup } = makeFakePackage(FIXED_INPUT);
+  it('the documented EXPECTED is the enumerate+normalize+sha256 of the tree', () => {
+    // Proves EXPECTED is not a magic constant but the documented computation — a
+    // local re-implementation of the loader's tree walk.
+    const { entry, cleanup } = makeFakePackage(CROSS_IMPL_TREE);
     try {
-      expect(computeSrcRegistryStamp(entry)).toBe(expected);
+      const srcDir = join(dirname(dirname(entry)), 'src');
+      const collect = (dir: string): string[] => {
+        const out: string[] = [];
+        for (const e of readdirSync(dir)) {
+          const f = join(dir, e);
+          if (statSync(f).isDirectory()) out.push(...collect(f));
+          else if (e.endsWith('.ts') && !e.endsWith('.generated.ts'))
+            out.push(f);
+        }
+        return out;
+      };
+      const files = collect(srcDir)
+        .map((abs) => ({ rel: relative(srcDir, abs).split(sep).join('/'), abs }))
+        .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+      const h = createHash('sha256');
+      for (const { rel, abs } of files) {
+        const n = readFileSync(abs, 'utf8')
+          .replace(/\r\n/g, '\n')
+          .replace(/\n$/, '');
+        h.update(rel, 'utf8');
+        h.update('\0', 'utf8');
+        h.update(n, 'utf8');
+        h.update('\0', 'utf8');
+      }
+      const localHash = h.digest('hex');
+      expect(computeSrcRegistryStamp(entry)).toBe(localHash);
+      expect(localHash).toBe(CROSS_IMPL_EXPECTED);
     } finally {
       cleanup();
     }
diff --git a/apps/server/src/core/ai-chat/tools/docmost-client.loader.ts b/apps/server/src/core/ai-chat/tools/docmost-client.loader.ts
index 24f16f6a..8029a239 100644
--- a/apps/server/src/core/ai-chat/tools/docmost-client.loader.ts
+++ b/apps/server/src/core/ai-chat/tools/docmost-client.loader.ts
@@ -1,6 +1,6 @@
 import { createHash } from 'node:crypto';
-import { existsSync, readFileSync } from 'node:fs';
-import { dirname, join } from 'node:path';
+import { existsSync, readdirSync, readFileSync, statSync } from 'node:fs';
+import { dirname, join, relative, sep } from 'node:path';
 import { pathToFileURL } from 'node:url';
 import type { DocmostClient, SharedToolSpec } from '@docmost/mcp';
 
@@ -191,33 +191,52 @@ interface DocmostMcpModule {
  * present. Returns the stamp string, or `null` when the source is absent (a prod
  * image ships only build/, no src/). MUST stay byte-for-byte identical to
  * packages/mcp/scripts/gen-registry-stamp.mjs's `computeRegistryStamp` so the
- * build-time and src-time hashes agree: same input file (src/tool-specs.ts), same
- * normalization (CRLF -> LF, strip a single trailing newline), same sha256.
+ * build-time and src-time hashes agree: same file set (every src/**\/*.ts except
+ * *.generated.ts), same POSIX-relative sort, same per-file normalization (CRLF ->
+ * LF, strip a single trailing newline) with the same path+content framing, same
+ * sha256. Hashing the WHOLE src tree (not just tool-specs.ts) is #486: an edit to
+ * client.ts / a client/* module / comment-signal / drawio-* without a rebuild
+ * must also be caught, otherwise build/ silently serves the old code.
  *
  * DEV vs PROD detection is by FILE EXISTENCE, not NODE_ENV: we resolve the
  * package's own directory from `require.resolve('@docmost/mcp')` (which points at
- * build/index.js) and look for ../src/tool-specs.ts next to it. In a dev/test
- * worktree that file exists; in a prod image (build/ only, src/ stripped) it does
- * not, so this returns null and the caller skips the check. Any error (ENOENT, a
- * bad resolve) is swallowed to null — the stale-check must NEVER break startup.
+ * build/index.js) and look for ../src next to it. In a dev/test worktree that
+ * directory exists; in a prod image (build/ only, src/ stripped) it does not, so
+ * this returns null and the caller skips the check. Any error (ENOENT, a bad
+ * resolve) is swallowed to null — the stale-check must NEVER break startup.
  *
  * Exported for unit testing (docmost-client.loader.spec.ts): the export keyword
  * is behaviourally a no-op — the module-internal caller `loadDocmostMcp` is
  * unaffected. The test drives the null (no-src) path and asserts this
- * normalize+sha256 stays identical to the codegen's `computeRegistryStamp`.
+ * enumerate+normalize+sha256 stays identical to the codegen's
+ * `computeRegistryStamp`.
  */
 export function computeSrcRegistryStamp(packageEntry: string): string | null {
   try {
     // packageEntry is <pkg>/build/index.js; the source lives at <pkg>/src/.
-    const toolSpecsPath = join(
-      dirname(dirname(packageEntry)),
-      'src',
-      'tool-specs.ts',
-    );
-    if (!existsSync(toolSpecsPath)) return null; // prod: no src tree -> skip.
-    const source = readFileSync(toolSpecsPath, 'utf8');
-    const normalized = source.replace(/\r\n/g, '\n').replace(/\n$/, '');
-    return createHash('sha256').update(normalized, 'utf8').digest('hex');
+    const srcDir = join(dirname(dirname(packageEntry)), 'src');
+    if (!existsSync(srcDir)) return null; // prod: no src tree -> skip.
+    // Enumerate every src/**\/*.ts except the codegen's own *.generated.ts
+    // output (including it would be a fixed-point cycle). Sort by POSIX-relative
+    // path so ordering is platform-independent, then fold each file's relative
+    // path + normalized content into one hash — identical to the codegen.
+    const files = collectStampFiles(srcDir)
+      .map((abs) => ({
+        rel: relative(srcDir, abs).split(sep).join('/'),
+        abs,
+      }))
+      .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+    const hash = createHash('sha256');
+    for (const { rel, abs } of files) {
+      const normalized = readFileSync(abs, 'utf8')
+        .replace(/\r\n/g, '\n')
+        .replace(/\n$/, '');
+      hash.update(rel, 'utf8');
+      hash.update('\0', 'utf8');
+      hash.update(normalized, 'utf8');
+      hash.update('\0', 'utf8');
+    }
+    return hash.digest('hex');
   } catch {
     // Never let a resolution/read hiccup break server startup — treat as "no
     // src available" and skip the check (identical to the prod no-op path).
@@ -225,6 +244,24 @@ export function computeSrcRegistryStamp(packageEntry: string): string | null {
   }
 }
 
+/**
+ * Recursively enumerate every `*.ts` under `dir`, EXCLUDING `*.generated.ts`.
+ * Mirror of the codegen's `collectStampFiles` (packages/mcp/scripts/
+ * gen-registry-stamp.mjs) — keep the two walk/filter rules identical.
+ */
+function collectStampFiles(dir: string): string[] {
+  const out: string[] = [];
+  for (const entry of readdirSync(dir)) {
+    const full = join(dir, entry);
+    if (statSync(full).isDirectory()) {
+      out.push(...collectStampFiles(full));
+    } else if (entry.endsWith('.ts') && !entry.endsWith('.generated.ts')) {
+      out.push(full);
+    }
+  }
+  return out;
+}
+
 // TS with module:commonjs downlevels a literal `import()` to `require()`, which
 // cannot load the ESM-only `@docmost/mcp` package. Indirect through Function so
 // the real dynamic `import()` survives compilation and can load ESM from
diff --git a/packages/mcp/scripts/gen-registry-stamp.mjs b/packages/mcp/scripts/gen-registry-stamp.mjs
index ecf865a5..82a559ab 100644
--- a/packages/mcp/scripts/gen-registry-stamp.mjs
+++ b/packages/mcp/scripts/gen-registry-stamp.mjs
@@ -1,60 +1,100 @@
 // Codegen: emit src/registry-stamp.generated.ts with a REGISTRY_STAMP hash of
-// the tool-specs REGISTRY CONTENT, so a build/ vs src/ skew (issue #447) is
-// detectable at runtime.
+// the ENTIRE src/ tree, so a build/ vs src/ skew (issue #447) is detectable at
+// runtime for ANY source file — not just tool-specs.ts.
 //
-// WHY hash the raw source text (not extracted structured data):
-// SHARED_TOOL_SPECS carries `buildShape` functions (the input SCHEMAS) which are
-// NOT serializable. The input schema is exactly one of the things that MUST stay
-// in sync between build/ and src/, so we cannot drop it from the hash. Rather
-// than probe zod with a fragile shim to reconstruct the schema shape, we hash the
-// STABLE, deterministic source TEXT of tool-specs.ts. That text fully captures
-// every field that must stay in sync — mcpName, inAppKey, description, tier,
-// catalogLine AND the buildShape bodies (input schemas) — with zero probing
-// fragility. Any edit to a spec (a renamed tool, a reworded description, a
-// changed schema field) changes the text and therefore the stamp.
+// WHY hash the whole src tree (not just tool-specs.ts): the runtime tools are
+// assembled from far more than the spec registry — client.ts, the client/*
+// domain modules, comment-signal.ts and the drawio-* helpers all ship in build/
+// and are loaded by the in-app server. Hashing ONLY tool-specs.ts meant an edit
+// to any of those (e.g. a behavioural fix in client.ts) left the stamp unchanged,
+// so a stale build/ served the OLD code silently (issue #486). Hashing every
+// src/**/*.ts closes that gap: any source edit changes the stamp.
 //
-// DETERMINISM: the hash is computed over the file bytes with line endings
-// normalized to LF and a single trailing newline stripped, so a CRLF checkout or
-// an editor's trailing-newline habit cannot make build/ and src/ disagree. No
-// Date.now / randomness. The loader's dev-only stale-check (docmost-client.loader.ts)
-// re-runs THIS SAME normalization + sha256 over src/tool-specs.ts and compares to
-// the built REGISTRY_STAMP; the two must compute identically.
+// WHY hash the raw source text (not extracted structured data): the tool input
+// SCHEMAS live as `buildShape` functions which are NOT serializable, so we cannot
+// reduce them to structured data without a fragile zod shim. Hashing the STABLE,
+// deterministic source TEXT captures every field that must stay in sync with zero
+// probing fragility. Any edit to any source file changes the text → the stamp.
+//
+// DETERMINISM: files are enumerated recursively, filtered to *.ts EXCLUDING
+// *.generated.ts (the codegen's OWN output — including it would create a
+// fixed-point cycle), and sorted by their POSIX-normalized path relative to src/
+// so the order is platform-independent. Each file contributes its relative path
+// AND its content with line endings normalized to LF and a single trailing
+// newline stripped, so a CRLF checkout or an editor's trailing-newline habit
+// cannot make build/ and src/ disagree. No Date.now / randomness. The loader's
+// dev-only stale-check (docmost-client.loader.ts) re-runs THIS SAME enumeration +
+// normalization + sha256 and compares to the built REGISTRY_STAMP; the two must
+// compute identically.
 //
 // This script runs from the `build` and `pretest` npm scripts BEFORE tsc, so
-// build/ always carries a stamp derived from the tool-specs.ts that was compiled.
+// build/ always carries a stamp derived from the src/ tree that was compiled.
 
 import { createHash } from 'node:crypto';
-import { readFileSync, writeFileSync } from 'node:fs';
+import { readdirSync, readFileSync, statSync, writeFileSync } from 'node:fs';
 import { fileURLToPath } from 'node:url';
-import { dirname, join } from 'node:path';
+import { dirname, join, relative, sep } from 'node:path';
 
 const __dirname = dirname(fileURLToPath(import.meta.url));
 const SRC_DIR = join(__dirname, '..', 'src');
-const TOOL_SPECS_PATH = join(SRC_DIR, 'tool-specs.ts');
 const OUT_PATH = join(SRC_DIR, 'registry-stamp.generated.ts');
 
 /**
- * Deterministic stamp of the tool-specs registry content. Kept as a plain
- * function (exported) so the algorithm has a single home; the loader duplicates
- * only the tiny normalize+sha256 steps because it lives in the CJS server build
- * and cannot import this ESM script. If you change the normalization here, mirror
- * it in apps/server/src/core/ai-chat/tools/docmost-client.loader.ts.
+ * Recursively enumerate every `*.ts` file under `dir`, EXCLUDING the codegen's
+ * own `*.generated.ts` output (a self-referential cycle otherwise). Returns
+ * absolute paths, unsorted (the caller sorts by relative path for determinism).
+ * Kept as a plain exported function so the algorithm has a single home; the
+ * loader duplicates it because it lives in the CJS server build and cannot import
+ * this ESM script. If you change the walk/filter here, mirror it in
+ * apps/server/src/core/ai-chat/tools/docmost-client.loader.ts.
  */
-export function computeRegistryStamp(toolSpecsSource) {
-  const normalized = toolSpecsSource.replace(/\r\n/g, '\n').replace(/\n$/, '');
-  return createHash('sha256').update(normalized, 'utf8').digest('hex');
+export function collectStampFiles(dir) {
+  const out = [];
+  for (const entry of readdirSync(dir)) {
+    const full = join(dir, entry);
+    if (statSync(full).isDirectory()) {
+      out.push(...collectStampFiles(full));
+    } else if (entry.endsWith('.ts') && !entry.endsWith('.generated.ts')) {
+      out.push(full);
+    }
+  }
+  return out;
+}
+
+/**
+ * Deterministic stamp of the whole src/ tree. Enumerate + sort by POSIX-relative
+ * path, then fold each file's relative path AND normalized content into one
+ * sha256. MUST stay byte-for-byte identical to the loader's recompute.
+ */
+export function computeRegistryStamp(srcDir) {
+  const files = collectStampFiles(srcDir)
+    .map((abs) => ({
+      rel: relative(srcDir, abs).split(sep).join('/'),
+      abs,
+    }))
+    .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+  const hash = createHash('sha256');
+  for (const { rel, abs } of files) {
+    const normalized = readFileSync(abs, 'utf8')
+      .replace(/\r\n/g, '\n')
+      .replace(/\n$/, '');
+    hash.update(rel, 'utf8');
+    hash.update('\0', 'utf8');
+    hash.update(normalized, 'utf8');
+    hash.update('\0', 'utf8');
+  }
+  return hash.digest('hex');
 }
 
 function main() {
-  const source = readFileSync(TOOL_SPECS_PATH, 'utf8');
-  const stamp = computeRegistryStamp(source);
+  const stamp = computeRegistryStamp(SRC_DIR);
   const out =
     '// AUTO-GENERATED by scripts/gen-registry-stamp.mjs — DO NOT EDIT BY HAND.\n' +
-    '// A deterministic hash of src/tool-specs.ts content (tool names, descriptions,\n' +
-    '// tiers, catalog lines and input schemas). Regenerated on every build/pretest\n' +
-    '// so build/ always matches the compiled src. The in-app loader recomputes this\n' +
-    '// from src and refuses to run on a mismatch (issue #447). This file is\n' +
-    '// gitignored and produced by the build — see .gitignore.\n' +
+    '// A deterministic hash of the whole src/ tree (every src/**/*.ts except\n' +
+    '// *.generated.ts). Regenerated on every build/pretest so build/ always\n' +
+    '// matches the compiled src. The in-app loader recomputes this from src and\n' +
+    '// refuses to run on a mismatch (issue #447/#486). This file is gitignored\n' +
+    '// and produced by the build — see .gitignore.\n' +
     `export const REGISTRY_STAMP = ${JSON.stringify(stamp)};\n`;
   writeFileSync(OUT_PATH, out, 'utf8');
   // eslint-disable-next-line no-console
diff --git a/packages/mcp/test/unit/registry-stamp.test.mjs b/packages/mcp/test/unit/registry-stamp.test.mjs
index b9d992c4..32006688 100644
--- a/packages/mcp/test/unit/registry-stamp.test.mjs
+++ b/packages/mcp/test/unit/registry-stamp.test.mjs
@@ -1,101 +1,220 @@
 import { test } from "node:test";
 import assert from "node:assert/strict";
-import { createHash } from "node:crypto";
-import { readFileSync } from "node:fs";
+import {
+  mkdtempSync,
+  mkdirSync,
+  writeFileSync,
+  rmSync,
+  readdirSync,
+  statSync,
+  readFileSync,
+} from "node:fs";
+import { tmpdir } from "node:os";
 import { fileURLToPath } from "node:url";
-import { dirname, join } from "node:path";
+import { dirname, join, relative, sep } from "node:path";
+import { createHash } from "node:crypto";
 
 import { computeRegistryStamp } from "../../scripts/gen-registry-stamp.mjs";
 import { REGISTRY_STAMP } from "../../build/index.js";
 
-// Guard tests for the build/src-skew stamp (issue #447). The codegen script
-// exports `computeRegistryStamp(sourceText)` — a sha256 over normalized source
-// text (CRLF->LF, single trailing newline stripped). The in-app loader
-// (apps/server/.../docmost-client.loader.ts) DUPLICATES that normalize+sha256 to
-// recompute the stamp from src and refuse a stale build. These tests pin the
-// algorithm's behaviour AND assert the built stamp matches the current src, so a
-// stale generated file OR a normalize divergence reddens.
+// Guard tests for the build/src-skew stamp (issues #447/#486). The codegen script
+// exports `computeRegistryStamp(srcDir)` — a sha256 over the WHOLE src/ tree
+// (every src/**/*.ts EXCEPT *.generated.ts), each file folded in as its
+// POSIX-relative path + its normalized content (CRLF->LF, single trailing newline
+// stripped). Hashing the whole tree (not just tool-specs.ts) is #486: an edit to
+// client.ts / a client/* module without a rebuild must ALSO redden. The in-app
+// loader (apps/server/.../docmost-client.loader.ts) DUPLICATES this enumerate+
+// normalize+sha256 to refuse a stale build. These tests pin the algorithm and
+// assert the built stamp matches the current src.
 
 const __dirname = dirname(fileURLToPath(import.meta.url));
-const TOOL_SPECS_PATH = join(__dirname, "..", "..", "src", "tool-specs.ts");
+const SRC_DIR = join(__dirname, "..", "..", "src");
 
-test("computeRegistryStamp is deterministic: same input -> same hash", () => {
-  const input = "export const X = 1;\nexport const Y = 2;\n";
-  assert.equal(computeRegistryStamp(input), computeRegistryStamp(input));
+// Build a throwaway src/ tree from a { relPath: content } map and return its dir.
+function makeSrcTree(files) {
+  const root = mkdtempSync(join(tmpdir(), "mcp-stamp-tree-"));
+  const src = join(root, "src");
+  for (const [rel, content] of Object.entries(files)) {
+    const full = join(src, rel);
+    mkdirSync(dirname(full), { recursive: true });
+    writeFileSync(full, content, "utf8");
+  }
+  return { src, cleanup: () => rmSync(root, { recursive: true, force: true }) };
+}
+
+test("computeRegistryStamp is deterministic: same tree -> same hash", () => {
+  const a = makeSrcTree({ "tool-specs.ts": "export const X = 1;\n" });
+  const b = makeSrcTree({ "tool-specs.ts": "export const X = 1;\n" });
+  try {
+    assert.equal(computeRegistryStamp(a.src), computeRegistryStamp(b.src));
+  } finally {
+    a.cleanup();
+    b.cleanup();
+  }
 });
 
 test("computeRegistryStamp returns a 64-char lowercase hex sha256", () => {
-  const stamp = computeRegistryStamp("anything");
-  assert.match(stamp, /^[0-9a-f]{64}$/);
+  const t = makeSrcTree({ "tool-specs.ts": "anything\n" });
+  try {
+    assert.match(computeRegistryStamp(t.src), /^[0-9a-f]{64}$/);
+  } finally {
+    t.cleanup();
+  }
 });
 
-test("normalizes CRLF vs LF: the same content hashes equal", () => {
-  const lf = "line1\nline2\nline3";
-  const crlf = "line1\r\nline2\r\nline3";
-  assert.equal(computeRegistryStamp(crlf), computeRegistryStamp(lf));
+// #486 CORE: an edit to a NON-tool-specs source file (client.ts) must change the
+// stamp. Under the old single-file (tool-specs.ts only) hash this edit was
+// invisible and a stale build/ served the old client.ts silently.
+test("editing client.ts (not tool-specs.ts) changes the stamp (#486)", () => {
+  const before = makeSrcTree({
+    "tool-specs.ts": "export const SPECS = 1;\n",
+    "client.ts": "export const impl = 'v1';\n",
+  });
+  const after = makeSrcTree({
+    "tool-specs.ts": "export const SPECS = 1;\n",
+    "client.ts": "export const impl = 'v2';\n",
+  });
+  try {
+    assert.notEqual(
+      computeRegistryStamp(before.src),
+      computeRegistryStamp(after.src),
+      "a client.ts edit with an unchanged tool-specs.ts must move the stamp",
+    );
+  } finally {
+    before.cleanup();
+    after.cleanup();
+  }
 });
 
-test("normalizes a trailing newline: with/without a final \\n hashes equal", () => {
-  const noTrailing = "alpha\nbeta";
-  const trailing = "alpha\nbeta\n";
-  assert.equal(computeRegistryStamp(trailing), computeRegistryStamp(noTrailing));
+test("editing a nested client/* module changes the stamp", () => {
+  const before = makeSrcTree({
+    "tool-specs.ts": "x\n",
+    "client/read.ts": "export const READ = 1;\n",
+  });
+  const after = makeSrcTree({
+    "tool-specs.ts": "x\n",
+    "client/read.ts": "export const READ = 2;\n",
+  });
+  try {
+    assert.notEqual(
+      computeRegistryStamp(before.src),
+      computeRegistryStamp(after.src),
+    );
+  } finally {
+    before.cleanup();
+    after.cleanup();
+  }
 });
 
-test("a CRLF checkout WITH a trailing CRLF still hashes equal to bare LF", () => {
-  // A worst-case Windows checkout: CRLF line endings + a trailing CRLF. Both the
-  // \r\n->\n replace and the trailing-newline strip must apply for parity.
-  const bare = "alpha\nbeta";
-  const crlfTrailing = "alpha\r\nbeta\r\n";
-  assert.equal(
-    computeRegistryStamp(crlfTrailing),
-    computeRegistryStamp(bare),
-  );
+// *.generated.ts is EXCLUDED (else the codegen's own output is a fixed-point
+// cycle): adding/removing/changing it must not move the stamp.
+test("*.generated.ts is excluded from the stamp", () => {
+  const without = makeSrcTree({ "tool-specs.ts": "x\n" });
+  const withGen = makeSrcTree({
+    "tool-specs.ts": "x\n",
+    "registry-stamp.generated.ts": 'export const REGISTRY_STAMP = "abc";\n',
+  });
+  try {
+    assert.equal(
+      computeRegistryStamp(without.src),
+      computeRegistryStamp(withGen.src),
+      "a *.generated.ts file must not affect the stamp",
+    );
+  } finally {
+    without.cleanup();
+    withGen.cleanup();
+  }
 });
 
-test("a real content change hashes differently", () => {
-  const before = "export const description = 'search a page';\n";
-  const after = "export const description = 'search a PAGE';\n";
-  assert.notEqual(computeRegistryStamp(before), computeRegistryStamp(after));
+test("a CRLF checkout WITH trailing CRLF hashes equal to bare LF", () => {
+  const bare = makeSrcTree({ "tool-specs.ts": "alpha\nbeta" });
+  const crlfTrailing = makeSrcTree({ "tool-specs.ts": "alpha\r\nbeta\r\n" });
+  try {
+    assert.equal(
+      computeRegistryStamp(crlfTrailing.src),
+      computeRegistryStamp(bare.src),
+    );
+  } finally {
+    bare.cleanup();
+    crlfTrailing.cleanup();
+  }
 });
 
-// Only a SINGLE trailing newline is stripped — a second blank line is content and
-// must change the hash. This pins the exact `/\n$/` semantics the loader mirrors.
+// Only a SINGLE trailing newline is stripped — a second blank line is content.
 test("only ONE trailing newline is stripped (two differ from one)", () => {
-  assert.notEqual(
-    computeRegistryStamp("x\n"),
-    computeRegistryStamp("x\n\n"),
-  );
+  const one = makeSrcTree({ "tool-specs.ts": "x\n" });
+  const two = makeSrcTree({ "tool-specs.ts": "x\n\n" });
+  try {
+    assert.notEqual(
+      computeRegistryStamp(one.src),
+      computeRegistryStamp(two.src),
+    );
+  } finally {
+    one.cleanup();
+    two.cleanup();
+  }
 });
 
-// Cross-impl equality against a fixed, documented input. The SAME literal input
-// and expected hash are asserted in the server-side jest test
-// (docmost-client.loader.spec.ts). If either side's normalize+sha256 ever
-// diverges, one of the two tests reddens. Input exercises BOTH normalize steps.
-test("fixed-input hash matches the documented cross-impl value", () => {
-  const FIXED_INPUT = "line1\r\nline2\n";
-  const EXPECTED =
-    "683376e290829b482c2655745caffa7a1dccfa10afaa62dac2b42dd6c68d0f83";
-  assert.equal(computeRegistryStamp(FIXED_INPUT), EXPECTED);
+// Cross-impl equality against a fixed, documented tree. The SAME literal tree and
+// expected hash are asserted in the server-side jest test
+// (docmost-client.loader.spec.ts). If either side's enumerate+normalize+sha256
+// ever diverges, one of the two tests reddens. The tree exercises: a nested file,
+// BOTH normalize steps (tool-specs.ts uses CRLF + trailing \n) and the
+// *.generated.ts exclusion.
+const CROSS_IMPL_TREE = {
+  "tool-specs.ts": "line1\r\nline2\n",
+  "client/read.ts": "export const R = 1;\n",
+  "registry-stamp.generated.ts": 'export const REGISTRY_STAMP="ignored";\n',
+};
+const CROSS_IMPL_EXPECTED =
+  "131c1b9e4e2f5a7d6cef91ca8df619822b442f52bc45ebd09474a4c1d6728616";
+
+test("fixed-tree hash matches the documented cross-impl value", () => {
+  const t = makeSrcTree(CROSS_IMPL_TREE);
+  try {
+    assert.equal(computeRegistryStamp(t.src), CROSS_IMPL_EXPECTED);
+  } finally {
+    t.cleanup();
+  }
 });
 
-// DESYNC GUARD (covers reviewer suggestion 2). Recompute the stamp from the
-// actual src/tool-specs.ts and assert it equals the REGISTRY_STAMP baked into the
-// freshly-built build/index.js. This reddens if the generated file is stale OR if
-// the codegen normalize ever diverges from what produced the built stamp.
-test("built REGISTRY_STAMP equals the stamp recomputed from src/tool-specs.ts", () => {
-  const source = readFileSync(TOOL_SPECS_PATH, "utf8");
-  assert.equal(computeRegistryStamp(source), REGISTRY_STAMP);
+// Sanity: the EXPECTED constant is not a magic value but the documented
+// enumerate+normalize+sha256 of CROSS_IMPL_TREE (a local re-implementation).
+test("the documented EXPECTED is the enumerate+normalize+sha256 of the tree", () => {
+  const t = makeSrcTree(CROSS_IMPL_TREE);
+  try {
+    const collect = (dir) => {
+      const out = [];
+      for (const e of readdirSync(dir)) {
+        const f = join(dir, e);
+        if (statSync(f).isDirectory()) out.push(...collect(f));
+        else if (e.endsWith(".ts") && !e.endsWith(".generated.ts")) out.push(f);
+      }
+      return out;
+    };
+    const files = collect(t.src)
+      .map((abs) => ({ rel: relative(t.src, abs).split(sep).join("/"), abs }))
+      .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+    const h = createHash("sha256");
+    for (const { rel, abs } of files) {
+      const n = readFileSync(abs, "utf8")
+        .replace(/\r\n/g, "\n")
+        .replace(/\n$/, "");
+      h.update(rel, "utf8");
+      h.update("\0", "utf8");
+      h.update(n, "utf8");
+      h.update("\0", "utf8");
+    }
+    assert.equal(h.digest("hex"), CROSS_IMPL_EXPECTED);
+  } finally {
+    t.cleanup();
+  }
 });
 
-// Sanity: the fixed-input helper computes the SAME way the codegen does, proving
-// the EXPECTED constant above is not an arbitrary magic value but the documented
-// normalize+sha256 of FIXED_INPUT. Belt-and-braces so a bad EXPECTED can't hide a
-// real regression.
-test("the documented EXPECTED constant is the normalize+sha256 of FIXED_INPUT", () => {
-  const FIXED_INPUT = "line1\r\nline2\n";
-  const normalized = FIXED_INPUT.replace(/\r\n/g, "\n").replace(/\n$/, "");
-  const expected = createHash("sha256")
-    .update(normalized, "utf8")
-    .digest("hex");
-  assert.equal(computeRegistryStamp(FIXED_INPUT), expected);
+// DESYNC GUARD. Recompute the stamp from the REAL src/ tree and assert it equals
+// the REGISTRY_STAMP baked into the freshly-built build/index.js. This reddens if
+// the generated file is stale OR if the codegen ever diverges from what produced
+// the built stamp.
+test("built REGISTRY_STAMP equals the stamp recomputed from src/", () => {
+  assert.equal(computeRegistryStamp(SRC_DIR), REGISTRY_STAMP);
 });