diff --git a/ansible_base/authentication/utils/claims.py b/ansible_base/authentication/utils/claims.py
index 8f2e21413..bdf9d95bb 100644
--- a/ansible_base/authentication/utils/claims.py
+++ b/ansible_base/authentication/utils/claims.py
@@ -562,21 +562,28 @@ def _process_user_value(
 
     evaluate_fn = operators[operator]
 
+    if not user_value:
+        _prefixed_debug(map_id, tracking_id, f"Attr [{attribute}] present but empty, skipping")
+        return has_access_with_join(has_access, False, join_condition)
+
+    per_attr_match = False
     for a_user_value in user_value:
         # Normalize user value for comparison
         user_str = f"{a_user_value}".casefold() if _is_case_insensitivity_enabled() else f"{a_user_value}"
 
         # Evaluate condition
         result = evaluate_fn(user_str, trigger_value)
-        has_access = has_access_with_join(has_access, result, join_condition)
 
         # Log result
         header = f"Attr [{attribute}] value [{user_str}]"
         message = _get_operator_messages(operator, result)
         _prefixed_debug(map_id, tracking_id, f"{header} {message} [{trigger_value}], {_result_suffix(result)}")
 
-    return has_access
+        if result:
+            per_attr_match = True
+            break
 
+    return has_access_with_join(has_access, per_attr_match, join_condition)
 
 def _result_suffix(result: bool) -> str:
     return "allowing" if result else "skipping"
diff --git a/pyproject.toml b/pyproject.toml
index 2a87db0bc..0fbdcb538 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -59,6 +59,8 @@ optional-dependencies.redis_client = { file = [ "requirements/requirements_redis
 optional-dependencies.oauth2_provider = { file = [ "requirements/requirements_oauth2_provider.in" ] }
 optional-dependencies.resource_registry = { file = [ "requirements/requirements_resource_registry.in" ] }
 optional-dependencies.feature_flags = { file = [ "requirements/requirements_feature_flags.in" ] }
+optional-dependencies.dev = { file = [ "requirements/requirements_dev.txt" ] }
+
 
 [build-system]
 requires = ["setuptools>=64", "setuptools_scm>=8"]
diff --git a/test_app/tests/authentication/utils/test_claims.py b/test_app/tests/authentication/utils/test_claims.py
index 41658db57..994ba64ee 100644
--- a/test_app/tests/authentication/utils/test_claims.py
+++ b/test_app/tests/authentication/utils/test_claims.py
@@ -747,8 +747,8 @@ def test_has_access_with_join(current_access, new_access, condition, expected):
             {"email": {"equals": "foo@example.com"}, "join_condition": "and"},
             {"email": ["bar@example.com", "foo@example.com"]},
             False,
-            claims.TriggerResult.SKIP,
-            id="user attribute is list, one match, explicit 'and', negative",
+            claims.TriggerResult.ALLOW,
+            id="user attribute is list, one match, explicit 'and', positive",
         ),
         pytest.param(
             {"email": {"equals": "foo@example.com"}, "join_condition": "and"},
@@ -911,6 +911,35 @@ def test_has_access_with_join(current_access, new_access, condition, expected):
             claims.TriggerResult.ALLOW,
             id="all attribute required by 'and' condition should result in allow",
         ),
+        pytest.param(
+            {
+                "cn": {"contains": "ldap"},
+                "employeeType": {"contains": "manager"},
+                "join_condition": "and",
+            },
+            {"cn": ["ldap_admin"], "employeeType": ["manager", "executor"]},
+            False,
+            claims.TriggerResult.ALLOW,
+            id="regression_any_semantics_and_across_attrs_positive",
+        ),
+        pytest.param(
+            {
+                "cn": {"contains": "ldap"},
+                "employeeType": {"contains": "manager"},
+                "join_condition": "and",
+            },
+            {"cn": ["ldap_admin"], "employeeType": ["executor"]},
+            False,
+            claims.TriggerResult.SKIP,
+            id="regression_any_semantics_and_across_attrs_negative",
+        ),
+        pytest.param(
+            {"cn": {"contains": "ldap"}, "employeeType": {"contains": "manager"}, "join_condition": "or"},
+            {"cn": ["zzz"], "employeeType": ["manager", "executor"]},
+            False,
+            claims.TriggerResult.ALLOW,
+            id="regression_any_semantics_or_across_attrs_positive_one_side",
+        ),
     ],
 )
 @pytest.mark.django_db