diff --git a/.cursor/rules/shipped-data-assets.mdc b/.cursor/rules/shipped-data-assets.mdc
new file mode 100644
index 0000000..75ba08e
--- /dev/null
+++ b/.cursor/rules/shipped-data-assets.mdc
@@ -0,0 +1,27 @@
+---
+description: Shipped data/ assets must be git-trackable so tool updates include them
+globs: "{.gitignore,data/**,gui/guide_tab.py,gui/main.py,tests/test_bundled_updates.py}"
+alwaysApply: false
+---
+
+# Shipped data/ and tool updates
+
+Tool auto-update downloads a **git branch archive**.
+Anything matched by `.gitignore` is omitted from that archive and never reaches users.
+
+## When adding or changing shipped defaults under `data/`
+
+- Add a negation under `.gitignore` (same pattern as skills/help):
+  - `!data/skills/**`
+  - `!data/help/**`
+  - `!data/vocab_base.txt`
+  - `!data/translation_contexts.json`
+- Do **not** rely on `UpdateThread.should_install` alone - ignored files never appear in the zip.
+- Extend `_SHIPPED_DATA_FILES` / `ShippedDataTrackingTests` in `tests/test_bundled_updates.py` when adding a new shipped path.
+- User-local files stay ignored/protected: `data/vocab.txt`, `data/last_update_sha.txt`, `data/wolf_*.json`.
+
+## Quick check
+
+```bash
+git check-ignore -- data/help/index.json   # must exit 1 (not ignored)
+```
diff --git a/.gitignore b/.gitignore
index 2688f4a..b42b45d 100644
--- a/.gitignore
+++ b/.gitignore
@@ -20,6 +20,7 @@ __pycache__
 !assets/engine_icons/**
 !.pre-commit-config.yaml
 !data/skills/**
+!data/help/**
 !data/vocab_base.txt
 !data/translation_contexts.json
 !requirements.txt
diff --git a/data/help/index.json b/data/help/index.json
new file mode 100644
index 0000000..d070352
--- /dev/null
+++ b/data/help/index.json
@@ -0,0 +1,37 @@
+[
+  {
+    "id": "welcome",
+    "title": "Welcome",
+    "file": "00-welcome.md"
+  },
+  {
+    "id": "requirements",
+    "title": "Requirements",
+    "file": "01-requirements.md"
+  },
+  {
+    "id": "quickstart",
+    "title": "Quick Start",
+    "file": "02-quickstart.md"
+  },
+  {
+    "id": "workflow-rpg",
+    "title": "Workflow: RPG Maker",
+    "file": "03-workflow-rpg.md"
+  },
+  {
+    "id": "workflow-wolf",
+    "title": "Workflow: WolfDawn",
+    "file": "04-workflow-wolf.md"
+  },
+  {
+    "id": "other-tabs",
+    "title": "Other Tabs",
+    "file": "05-other-tabs.md"
+  },
+  {
+    "id": "examples",
+    "title": "Example Walkthrough",
+    "file": "06-examples.md"
+  }
+]
diff --git a/gui/main.py b/gui/main.py
index 0ac0b60..6723bad 100644
--- a/gui/main.py
+++ b/gui/main.py
@@ -78,8 +78,8 @@ class UpdateThread(QThread):
     PROTECTED_TOP = {".env", "venv", "log", "files", "translated"}
 
     # User-local files under data/ that must not be overwritten.
-    # Shipped defaults (translation_contexts.json, skills/*.md, vocab_base.txt, …)
-    # are intentionally updated so tool releases refresh prompts and contexts.
+    # Shipped defaults (translation_contexts.json, skills/*.md, help/*, vocab_base.txt, …)
+    # are intentionally updated so tool releases refresh prompts, Guide docs, and contexts.
     PROTECTED_DATA_FILES = frozenset({
         "data/vocab.txt",
         "data/last_update_sha.txt",
diff --git a/tests/test_bundled_updates.py b/tests/test_bundled_updates.py
index 348be83..b6054e6 100644
--- a/tests/test_bundled_updates.py
+++ b/tests/test_bundled_updates.py
@@ -7,6 +7,7 @@ a maintainer explicitly uses --force / --refresh-offline / --refresh-all.
 
 from __future__ import annotations
 
+import subprocess
 import tempfile
 import unittest
 from pathlib import Path
@@ -14,6 +15,19 @@ from unittest.mock import patch
 
 from util.wolfdawn import WolfDawnError, bundled_binary_path, ensure_wolf_binary
 
+_REPO_ROOT = Path(__file__).resolve().parents[1]
+
+# Shipped with tool updates from the git archive. Keep in sync with .gitignore
+# exceptions under data/ — ignored files never appear in update zips.
+_SHIPPED_DATA_FILES = (
+    "data/translation_contexts.json",
+    "data/skills/system.md",
+    "data/skills/project_setup.md",
+    "data/help/index.json",
+    "data/help/00-welcome.md",
+    "data/vocab_base.txt",
+)
+
 
 class UpdateThreadInstallFilterTests(unittest.TestCase):
     """Tool update must refresh shipped data/ assets while protecting user state."""
@@ -22,12 +36,7 @@ class UpdateThreadInstallFilterTests(unittest.TestCase):
         from gui.main import UpdateThread
 
         for rel in (
-            "data/translation_contexts.json",
-            "data/skills/system.md",
-            "data/skills/project_setup.md",
-            "data/help/index.json",
-            "data/help/00-welcome.md",
-            "data/vocab_base.txt",
+            *_SHIPPED_DATA_FILES,
             "gui/main.py",
             "gameupdate/GameUpdate.bat",
             "gameupdate/gameupdate/patch.ps1",
@@ -53,6 +62,62 @@ class UpdateThreadInstallFilterTests(unittest.TestCase):
                 self.assertFalse(UpdateThread.should_install(Path(rel)))
 
 
+class ShippedDataTrackingTests(unittest.TestCase):
+    """Guide/help and other shipped data/ files must be git-trackable.
+
+    Tool updates download a branch archive from git. Anything matched by
+    .gitignore is omitted from that archive, so Guide markdown and index.json
+    would never reach end users.
+    """
+
+    def test_shipped_data_files_exist(self):
+        for rel in _SHIPPED_DATA_FILES:
+            with self.subTest(rel=rel):
+                self.assertTrue(
+                    (_REPO_ROOT / rel).is_file(),
+                    f"missing shipped asset {rel}",
+                )
+
+    def test_help_dir_markdown_matches_index(self):
+        import json
+
+        help_dir = _REPO_ROOT / "data" / "help"
+        index = json.loads((help_dir / "index.json").read_text(encoding="utf-8"))
+        for entry in index:
+            rel = entry["file"]
+            with self.subTest(file=rel):
+                self.assertTrue(
+                    (help_dir / rel).is_file(),
+                    f"data/help/index.json references missing {rel}",
+                )
+
+    def test_shipped_data_files_are_not_gitignored(self):
+        help_dir = _REPO_ROOT / "data" / "help"
+        rels = list(_SHIPPED_DATA_FILES)
+        for path in sorted(help_dir.glob("*.md")):
+            rel = path.relative_to(_REPO_ROOT).as_posix()
+            if rel not in rels:
+                rels.append(rel)
+
+        for rel in rels:
+            with self.subTest(rel=rel):
+                # Plain check-ignore (no -v): exit 0 = ignored, 1 = not ignored.
+                # -v also reports negation rules with exit 0, which is a false positive.
+                result = subprocess.run(
+                    ["git", "check-ignore", "--", rel],
+                    cwd=_REPO_ROOT,
+                    capture_output=True,
+                    text=True,
+                    check=False,
+                )
+                self.assertNotEqual(
+                    result.returncode,
+                    0,
+                    f"{rel} is gitignored; "
+                    "add a !.gitignore exception under data/ so tool updates include it",
+                )
+
+
 class CheckToolUpdateTests(unittest.TestCase):
     """Tool update check compares remote SHA to data/last_update_sha.txt only."""