diff --git a/lib/ansible/playbook/conditional.py b/lib/ansible/playbook/conditional.py
index 874ba341855..0e846240dc7 100644
--- a/lib/ansible/playbook/conditional.py
+++ b/lib/ansible/playbook/conditional.py
@@ -92,10 +92,6 @@ class Conditional:
             ds = getattr(self, '_ds')
 
         try:
-            # this allows for direct boolean assignments to conditionals "when: False"
-            if isinstance(self.when, bool):
-                return self.when
-
             for conditional in self.when:
                 if not self._check_conditional(conditional, templar, all_vars):
                     return False
@@ -117,6 +113,10 @@ class Conditional:
         if conditional is None or conditional == '':
             return True
 
+        # this allows for direct boolean assignments to conditionals "when: False"
+        if isinstance(conditional, bool):
+            return conditional
+
         if templar.is_template(conditional):
             display.warning('when statements should not include jinja2 '
                             'templating delimiters such as {{ }} or {%% %%}. '
diff --git a/test/units/playbook/test_conditional.py b/test/units/playbook/test_conditional.py
index 4e392843fd6..668a66c7477 100644
--- a/test/units/playbook/test_conditional.py
+++ b/test/units/playbook/test_conditional.py
@@ -1,6 +1,7 @@
 
 from units.compat import unittest
 from units.mock.loader import DictDataLoader
+from units.compat.mock import MagicMock
 
 from ansible.plugins.strategy import SharedPluginLoaderObj
 from ansible.template import Templar
@@ -33,6 +34,20 @@ class TestConditional(unittest.TestCase):
         ret = self._eval_con(when, {})
         self.assertTrue(ret)
 
+    def test_true_boolean(self):
+        self.cond.when = [True]
+        m = MagicMock()
+        ret = self.cond.evaluate_conditional(m, {})
+        self.assertTrue(ret)
+        self.assertFalse(m.is_template.called)
+
+    def test_false_boolean(self):
+        self.cond.when = [False]
+        m = MagicMock()
+        ret = self.cond.evaluate_conditional(m, {})
+        self.assertFalse(ret)
+        self.assertFalse(m.is_template.called)
+
     def test_undefined(self):
         when = [u"{{ some_undefined_thing }}"]
         self.assertRaisesRegexp(errors.AnsibleError, "The conditional check '{{ some_undefined_thing }}' failed",