diff --git a/test/test_web_api.py b/test/test_web_api.py
index 91cdd3bd..e8f57bea 100644
--- a/test/test_web_api.py
+++ b/test/test_web_api.py
@@ -433,6 +433,9 @@ class TestPluginsAPI:
         # Missing either side yields no signal.
         assert _is_plugin_update_available('', '1.0.0') is False
         assert _is_plugin_update_available('1.0.0', '') is False
+        # Unparseable version differing from the installed one surfaces the
+        # mismatch rather than hiding a possible update.
+        assert _is_plugin_update_available('1.0.0', 'not-a-semver') is True
 
     def test_get_plugin_health(self, client, mock_plugin_manager):
         """Test getting plugin health information."""
diff --git a/web_interface/blueprints/api_v3.py b/web_interface/blueprints/api_v3.py
index 73d16ade..41631ef1 100644
--- a/web_interface/blueprints/api_v3.py
+++ b/web_interface/blueprints/api_v3.py
@@ -134,9 +134,15 @@ def _is_plugin_update_available(installed_version: str, latest_version: str) ->
     if installed_version == latest_version:
         return False
     try:
-        from packaging.version import parse as _parse_version
+        from packaging.version import parse as _parse_version, InvalidVersion
+    except ImportError:
+        # packaging is a core dependency, but if it's somehow unavailable we
+        # can't compare semantically — surface the mismatch we already know
+        # exists (the two strings differ).
+        return True
+    try:
         return _parse_version(latest_version) > _parse_version(installed_version)
-    except Exception:
+    except InvalidVersion:
         # Unparseable version string: we can't tell direction, so surface the
         # mismatch rather than silently hiding a potential update.
         return True