diff --git a/changelogs/fragments/truthiness-tests.yaml b/changelogs/fragments/truthiness-tests.yaml
new file mode 100644
index 00000000000..303c7a9ed93
--- /dev/null
+++ b/changelogs/fragments/truthiness-tests.yaml
@@ -0,0 +1,2 @@
+minor_changes:
+- tests - Add new ``truthy`` and ``falsy`` jinja2 tests to evaluate the truthiness or falsiness of a value
diff --git a/docs/docsite/rst/user_guide/playbooks_tests.rst b/docs/docsite/rst/user_guide/playbooks_tests.rst
index 1dd8bdd6cf1..986325823ce 100644
--- a/docs/docsite/rst/user_guide/playbooks_tests.rst
+++ b/docs/docsite/rst/user_guide/playbooks_tests.rst
@@ -61,6 +61,46 @@ To match strings against a substring or a regular expression, use the "match", "
 
 'match' requires zero or more characters at the beginning of the string, while 'search' only requires matching a subset of the string. By default, 'regex' works like `search`, but `regex` can be configured to perform other tests as well.
 
+.. _testing_truthiness:
+
+Testing Truthiness
+``````````````````
+
+.. versionadded:: 2.10
+
+As of Ansible 2.10, you can now perform Python like truthy and falsy checks.
+
+.. code-block:: yaml
+
+    - debug:
+        msg: "Truthy"
+      when: value is truthy
+      vars:
+        value: "some string"
+
+    - debug:
+        msg: "Falsy"
+      when: value is falsy
+      vars:
+        value: ""
+
+Additionally, the ``truthy`` and ``falsy`` tests accept an optional parameter called ``convert_bool`` that will attempt
+to convert boolean indicators to actual booleans.
+
+.. code-block:: yaml
+
+    - debug:
+        msg: "Truthy"
+      when: value is truthy(convert_bool=True)
+      vars:
+        value: "yes"
+
+    - debug:
+        msg: "Falsy"
+      when: value is falsy(convert_bool=True)
+      vars:
+        value: "off"
+
 .. _testing_versions:
 
 Version Comparison
diff --git a/lib/ansible/plugins/test/core.py b/lib/ansible/plugins/test/core.py
index 66aff2a14bf..f88a5d931b6 100644
--- a/lib/ansible/plugins/test/core.py
+++ b/lib/ansible/plugins/test/core.py
@@ -26,6 +26,7 @@ from distutils.version import LooseVersion, StrictVersion
 from ansible import errors
 from ansible.module_utils._text import to_text
 from ansible.module_utils.common._collections_compat import MutableMapping, MutableSequence
+from ansible.module_utils.parsing.convert_bool import boolean
 from ansible.utils.display import Display
 
 display = Display()
@@ -165,6 +166,34 @@ def version_compare(value, version, operator='eq', strict=False):
         raise errors.AnsibleFilterError('Version comparison: %s' % e)
 
 
+def truthy(value, convert_bool=False):
+    """Evaluate as value for truthiness using python ``bool``
+
+    Optionally, attempt to do a conversion to bool from boolean like values
+    such as ``"false"``, ``"true"``, ``"yes"``, ``"no"``, ``"on"``, ``"off"``, etc.
+
+    .. versionadded:: 2.10
+    """
+    if convert_bool:
+        try:
+            value = boolean(value)
+        except TypeError:
+            pass
+
+    return bool(value)
+
+
+def falsy(value, convert_bool=False):
+    """Evaluate as value for falsiness using python ``bool``
+
+    Optionally, attempt to do a conversion to bool from boolean like values
+    such as ``"false"``, ``"true"``, ``"yes"``, ``"no"``, ``"on"``, ``"off"``, etc.
+
+    .. versionadded:: 2.10
+    """
+    return not truthy(value, convert_bool=convert_bool)
+
+
 class TestModule(object):
     ''' Ansible core jinja2 tests '''
 
@@ -203,4 +232,8 @@ class TestModule(object):
             # lists
             'any': any,
             'all': all,
+
+            # truthiness
+            'truthy': truthy,
+            'falsy': falsy,
         }
diff --git a/test/integration/targets/tests/aliases b/test/integration/targets/tests/aliases
new file mode 100644
index 00000000000..69e3eebcfc3
--- /dev/null
+++ b/test/integration/targets/tests/aliases
@@ -0,0 +1,2 @@
+shippable/posix/group2
+skip/python2.6  # tests are controller only, and we no longer support Python 2.6 on the controller
diff --git a/test/integration/targets/tests/tasks/main.yml b/test/integration/targets/tests/tasks/main.yml
new file mode 100644
index 00000000000..739675066ce
--- /dev/null
+++ b/test/integration/targets/tests/tasks/main.yml
@@ -0,0 +1,35 @@
+- name: Assert truthy tests work
+  assert:
+    that:
+      - '"string" is truthy'
+      - '"" is not truthy'
+      - True is truthy
+      - False is not truthy
+      - true is truthy
+      - false is not truthy
+      - 1 is truthy
+      - 0 is not truthy
+      - '[""] is truthy'
+      - '[] is not truthy'
+      - '"on" is truthy(convert_bool=True)'
+      - '"off" is not truthy(convert_bool=True)'
+      - '{} is not truthy'
+      - '{"key": "value"} is truthy'      
+
+- name: Assert falsy tests work
+  assert:
+    that:
+      - '"string" is not falsy'
+      - '"" is falsy'
+      - True is not falsy
+      - False is falsy
+      - true is not falsy
+      - false is falsy
+      - 1 is not falsy
+      - 0 is falsy
+      - '[""] is not falsy'
+      - '[] is falsy'
+      - '"on" is not falsy(convert_bool=True)'
+      - '"off" is falsy(convert_bool=True)'
+      - '{} is falsy'
+      - '{"key": "value"} is not falsy'