diff --git a/docs/genhhk.py b/docs/genhhk.py
new file mode 100644
index 000000000..f699a09ca
--- /dev/null
+++ b/docs/genhhk.py
@@ -0,0 +1,107 @@
+# -*- coding: utf-8 -*-
+"""Generate the .hhk keyword index for the CHM build.
+
+Sphinx's htmlhelp builder writes an empty x64dbgdoc.hhk because the docs
+don't use index directives. This script fills it with one entry per page,
+keyed by the page's <title>, so the CHM gets a usable Index tab.
+
+Usage: python genhhk.py _build/htmlhelp/x64dbgdoc.hhp
+Compatible with Python 2.7 (the portable build) and Python 3.
+"""
+
+from __future__ import print_function, unicode_literals
+
+import io
+import os
+import re
+import sys
+
+TITLE_RE = re.compile(r"<title>(.*?)</title>", re.IGNORECASE | re.DOTALL)
+
+ENTRY = (
+    '<LI> <OBJECT type="text/sitemap">\n'
+    '<param name="Name" value="{0}">\n'
+    '<param name="Local" value="{1}">\n'
+    "</OBJECT>\n"
+)
+
+
+def parse_files_section(hhp_path):
+    files = []
+    in_files = False
+    with io.open(hhp_path, "r", encoding="utf-8") as f:
+        for line in f:
+            line = line.strip()
+            if line.startswith("["):
+                in_files = line == "[FILES]"
+                continue
+            if in_files and line:
+                files.append(line)
+    return files
+
+
+def extract_title(html_path):
+    with io.open(html_path, "rb") as f:
+        data = f.read()
+    # Sphinx (py2) occasionally emits cp1252 bytes in files declared utf-8
+    try:
+        text = data.decode("utf-8")
+    except UnicodeDecodeError:
+        text = data.decode("cp1252")
+    match = TITLE_RE.search(text)
+    if not match:
+        return None
+    return " ".join(match.group(1).split())
+
+
+def escape_value(text):
+    # Pure-ASCII output so hhc.exe (ANSI) and pyhhc agree on the encoding
+    out = []
+    for ch in text:
+        if ch == '"':
+            out.append("&quot;")
+        elif ord(ch) > 126:
+            out.append("&#{0};".format(ord(ch)))
+        else:
+            out.append(ch)
+    return "".join(out)
+
+
+def main():
+    if len(sys.argv) != 2:
+        print("Usage: genhhk.py <project.hhp>")
+        return 1
+
+    hhp_path = sys.argv[1]
+    base_dir = os.path.dirname(os.path.abspath(hhp_path))
+    hhk_path = os.path.splitext(hhp_path)[0] + ".hhk"
+
+    entries = []
+    for rel in parse_files_section(hhp_path):
+        if not rel.lower().endswith((".htm", ".html")):
+            continue
+        html_path = os.path.join(base_dir, rel.replace("\\", os.sep))
+        if not os.path.isfile(html_path):
+            print("warning: missing file: " + rel)
+            continue
+        title = extract_title(html_path)
+        if not title:
+            print("warning: no <title> in: " + rel)
+            continue
+        local = rel.replace("\\", "/")
+        entries.append((title, local))
+
+    entries.sort(key=lambda e: (e[0].lower(), e[1]))
+
+    with io.open(hhk_path, "w", encoding="utf-8", newline="\n") as f:
+        f.write("<UL>\n")
+        for title, local in entries:
+            f.write(ENTRY.format(escape_value(title), local))
+        f.write("</UL>\n")
+
+    print("Wrote {0} index entries to {1}".format(len(entries), hhk_path))
+    return 0
+
+
+if __name__ == "__main__":
+    sys.exit(main())
diff --git a/docs/makechm.bat b/docs/makechm.bat
index 615696dd0..9f0c8222a 100644
--- a/docs/makechm.bat
+++ b/docs/makechm.bat
@@ -41,6 +41,9 @@ if %ERRORLEVEL% neq 0 exit /b %ERRORLEVEL%
 echo Applying CHM hacks
 copy theme.js .\_build\htmlhelp\_static\js\theme.js
 type hacks.css >> .\_build\htmlhelp\_static\css\theme.css
+echo Generating keyword index
+"%PORTABLE_PYTHON%\python.exe" genhhk.py .\_build\htmlhelp\x64dbgdoc.hhp
+if %ERRORLEVEL% neq 0 exit /b %ERRORLEVEL%
 echo Building CHM File
 hhc.exe .\_build\htmlhelp\x64dbgdoc.hhp
 copy /Y .\_build\htmlhelp\x64dbgdoc.chm x64dbg.chm