diff --git a/.github/windowdesc-ini-key.py b/.github/windowdesc-ini-key.py
new file mode 100644
--- /dev/null
+++ b/.github/windowdesc-ini-key.py
@@ -0,0 +1,50 @@
+"""
+Script to scan the OpenTTD source-tree for ini_key issues in WindowDesc entries.
+"""
+
+import glob
+import os
+import re
+import sys
+
+
+def scan_source_files(path, ini_keys=None):
+    if ini_keys is None:
+        ini_keys = set()
+
+    errors = []
+
+    for new_path in glob.glob(f"{path}/*.cpp"):
+        if os.path.isdir(new_path):
+            errors.append(scan_source_files(new_path, ini_keys))
+            continue
+
+        with open(new_path) as fp:
+            output = fp.read()
+
+        for (name, ini_key, widgets) in re.findall(r"^static WindowDesc ([a-zA-Z0-9_]*).*?, (?:\"(.*?)\")?.*?,(?:\s+(.*?),){6}", output, re.S|re.M):
+            if ini_key:
+                if ini_key in ini_keys:
+                    errors.append(f"{new_path}: {name} ini_key is a duplicate")
+                ini_keys.add(ini_key)
+            widget = re.findall("static const (?:struct )?NWidgetPart " + widgets + ".*?(?:WWT_(DEFSIZE|STICKY)BOX.*?)?;", output, re.S)[0]
+            if widget and not ini_key:
+                errors.append(f"{new_path}: {name} has WWT_DEFSIZEBOX/WWT_STICKYBOX without ini_key")
+            if ini_key and not widget:
+                errors.append(f"{new_path}: {name} has ini_key without WWT_DEFSIZEBOX/WWT_STICKYBOX")
+
+    return errors
+
+
+def main():
+    errors = scan_source_files("src")
+
+    if errors:
+        print("\n".join(errors))
+        sys.exit(1)
+
+    print("OK")
+
+
+if __name__ == "__main__":
+    main()
diff --git a/.github/workflows/windowdesc-ini-key.yml b/.github/workflows/windowdesc-ini-key.yml
new file mode 100644
--- /dev/null
+++ b/.github/workflows/windowdesc-ini-key.yml
@@ -0,0 +1,24 @@
+name: WindowDesc ini_key
+
+on:
+  pull_request:
+    branches:
+    - master
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref }}
+  cancel-in-progress: ${{ github.ref != 'refs/heads/master' }}
+
+jobs:
+  windowdesc-ini-key:
+    name: WindowDesc ini_key issues
+    runs-on: ubuntu-latest
+
+    steps:
+    - name: Checkout
+      uses: actions/checkout@v3
+
+    - name: Check for ini_key issues in WindowDesc entries
+      shell: bash
+      run: |
+        python3 .github/windowdesc-ini-key.py