diff --git a/plugins/hookify/core/config_loader.py b/plugins/hookify/core/config_loader.py
index fa2fc3e36f..d31f717c28 100644
--- a/plugins/hookify/core/config_loader.py
+++ b/plugins/hookify/core/config_loader.py
@@ -12,6 +12,76 @@
 from dataclasses import dataclass, field
 
 
+BOOLEAN_TRUE_VALUES = {'true', 'yes', 'on', '1'}
+BOOLEAN_FALSE_VALUES = {'false', 'no', 'off', '0'}
+BOOLEAN_FRONTMATTER_FIELDS = {'enabled'}
+
+
+def _strip_inline_comment(value: str) -> str:
+    """Remove an unquoted YAML-style inline comment from a scalar value."""
+    in_single_quote = False
+    in_double_quote = False
+
+    for index, char in enumerate(value):
+        if char == "'" and not in_double_quote:
+            in_single_quote = not in_single_quote
+        elif char == '"' and not in_single_quote:
+            in_double_quote = not in_double_quote
+        elif (
+            char == '#'
+            and not in_single_quote
+            and not in_double_quote
+            and (index == 0 or value[index - 1].isspace())
+        ):
+            return value[:index].rstrip()
+
+    return value
+
+
+def _strip_quotes(value: str) -> str:
+    """Strip the simple wrapping quotes supported by the frontmatter parser."""
+    return value.strip('"').strip("'")
+
+
+def _parse_boolean(value: Any, field_name: str = 'enabled') -> bool:
+    """Parse a boolean frontmatter field using common YAML spellings."""
+    if isinstance(value, bool):
+        return value
+
+    if isinstance(value, int) and not isinstance(value, bool):
+        if value in (0, 1):
+            return bool(value)
+
+    if isinstance(value, str):
+        normalized = _strip_quotes(_strip_inline_comment(value.strip())).strip().lower()
+        if normalized in BOOLEAN_TRUE_VALUES:
+            return True
+        if normalized in BOOLEAN_FALSE_VALUES:
+            return False
+
+    raise ValueError(
+        f"{field_name} must be a boolean "
+        "(true/false, yes/no, on/off, or 1/0)"
+    )
+
+
+def _parse_frontmatter_scalar(key: str, value: str) -> Any:
+    """Parse a top-level frontmatter scalar value."""
+    value = value.strip()
+
+    if key in BOOLEAN_FRONTMATTER_FIELDS:
+        return _parse_boolean(value, key)
+
+    value = _strip_quotes(value)
+
+    # Preserve the parser's historical true/false handling for other fields.
+    if value.lower() == 'true':
+        return True
+    if value.lower() == 'false':
+        return False
+    return value
+
+
 @dataclass
 class Condition:
     """A single condition for matching."""
@@ -74,7 +144,7 @@ def from_dict(cls, frontmatter: Dict[str, Any], message: str) -> 'Rule':
 
         return cls(
             name=frontmatter.get('name', 'unnamed'),
-            enabled=frontmatter.get('enabled', True),
+            enabled=_parse_boolean(frontmatter.get('enabled', True)),
             event=frontmatter.get('event', 'all'),
             pattern=simple_pattern,
             conditions=conditions,
@@ -144,12 +214,7 @@ def extract_frontmatter(content: str) -> tuple[Dict[str, Any], str]:
                 current_list = []
             else:
                 # Simple key-value pair
-                value = value.strip('"').strip("'")
-                if value.lower() == 'true':
-                    value = True
-                elif value.lower() == 'false':
-                    value = False
-                frontmatter[key] = value
+                frontmatter[key] = _parse_frontmatter_scalar(key, value)
 
         # List item (starts with -)
         elif stripped.startswith('-') and in_list:
diff --git a/plugins/hookify/tests/test_config_loader.py b/plugins/hookify/tests/test_config_loader.py
new file mode 100644
index 0000000000..d3c363f43d
--- /dev/null
+++ b/plugins/hookify/tests/test_config_loader.py
@@ -0,0 +1,92 @@
+#!/usr/bin/env python3
+
+import os
+import sys
+import tempfile
+import unittest
+from pathlib import Path
+
+
+sys.path.insert(0, str(Path(__file__).resolve().parents[2]))
+
+from hookify.core.config_loader import Rule, extract_frontmatter, load_rules  # noqa: E402
+
+
+def rule_for_enabled(value):
+    frontmatter, message = extract_frontmatter(
+        f"---\n"
+        f"name: r\n"
+        f"enabled: {value}\n"
+        f"event: bash\n"
+        f"pattern: rm -rf\n"
+        f"---\n"
+        f"msg\n"
+    )
+    return frontmatter, Rule.from_dict(frontmatter, message)
+
+
+class ConfigLoaderEnabledTest(unittest.TestCase):
+    def test_disabled_boolean_spellings_parse_false(self):
+        disabled_values = [
+            "no", "No", "NO",
+            "false", "False", "FALSE",
+            "off", "Off", "OFF",
+            "0",
+        ]
+
+        for value in disabled_values:
+            with self.subTest(value=value):
+                frontmatter, rule = rule_for_enabled(value)
+
+                self.assertIs(frontmatter["enabled"], False)
+                self.assertIs(rule.enabled, False)
+
+    def test_enabled_boolean_spellings_parse_true(self):
+        enabled_values = [
+            "yes", "Yes", "YES",
+            "true", "True", "TRUE",
+            "on", "On", "ON",
+            "1",
+        ]
+
+        for value in enabled_values:
+            with self.subTest(value=value):
+                frontmatter, rule = rule_for_enabled(value)
+
+                self.assertIs(frontmatter["enabled"], True)
+                self.assertIs(rule.enabled, True)
+
+    def test_inline_comment_is_ignored_for_enabled(self):
+        frontmatter, rule = rule_for_enabled("no # disabled for now")
+
+        self.assertIs(frontmatter["enabled"], False)
+        self.assertIs(rule.enabled, False)
+
+    def test_invalid_enabled_value_is_rejected(self):
+        with self.assertRaises(ValueError):
+            rule_for_enabled("maybe")
+
+    def test_load_rules_omits_enabled_no_rule(self):
+        previous_cwd = os.getcwd()
+        with tempfile.TemporaryDirectory() as temp_dir:
+            rule_dir = Path(temp_dir) / ".claude"
+            rule_dir.mkdir()
+            (rule_dir / "hookify.disabled.local.md").write_text(
+                "---\n"
+                "name: disabled\n"
+                "enabled: no\n"
+                "event: bash\n"
+                "pattern: rm -rf\n"
+                "---\n"
+                "msg\n"
+            )
+
+            try:
+                os.chdir(temp_dir)
+                self.assertEqual(load_rules(event="bash"), [])
+            finally:
+                os.chdir(previous_cwd)
+
+
+if __name__ == "__main__":
+    unittest.main()