diff --git a/changelogs/fragments/56017-allow-lazy-eval-on-jinja2-expr.yml b/changelogs/fragments/56017-allow-lazy-eval-on-jinja2-expr.yml
new file mode 100644
index 00000000000..e2fae50bde6
--- /dev/null
+++ b/changelogs/fragments/56017-allow-lazy-eval-on-jinja2-expr.yml
@@ -0,0 +1,2 @@
+breaking_changes:
+  - Allow for lazy evaluation of Jinja2 expressions (https://github.com/ansible/ansible/issues/56017)
diff --git a/docs/docsite/rst/porting_guides/porting_guide_core_2.14.rst b/docs/docsite/rst/porting_guides/porting_guide_core_2.14.rst
index af833303211..6e0cf9bca0d 100644
--- a/docs/docsite/rst/porting_guides/porting_guide_core_2.14.rst
+++ b/docs/docsite/rst/porting_guides/porting_guide_core_2.14.rst
@@ -19,7 +19,19 @@ This document is part of a collection on porting. The complete list of porting g
 Playbook
 ========
 
-No notable changes
+* Variables are now evaluated lazily; only when they are actually used. For example, in ansible-core 2.14 an expression ``{{ defined_variable or undefined_variable }}`` does not fail on ``undefined_variable`` if the first part of ``or`` is evaluated to ``True`` as it is not needed to evaluate the second part. One particular case of a change in behavior to note is the task below which uses the ``undefined`` test. Prior to version 2.14 this would result in a fatal error trying to access the undefined value in the dictionary. In 2.14 the assertion passes as the dictionary is evaluated as undefined through one of its undefined values:
+
+ .. code-block:: yaml
+
+     - assert:
+         that:
+           - some_defined_dict_with_undefined_values is undefined
+       vars:
+         dict_value: 1
+         some_defined_dict_with_undefined_values:
+           key1: value1
+           key2: '{{ dict_value }}'
+           key3: '{{ undefined_dict_value }}'
 
 
 Command Line
diff --git a/lib/ansible/template/vars.py b/lib/ansible/template/vars.py
index b91638f25d9..be2af9fc3b8 100644
--- a/lib/ansible/template/vars.py
+++ b/lib/ansible/template/vars.py
@@ -97,7 +97,15 @@ class AnsibleJ2Vars(Mapping):
             try:
                 value = self._templar.template(variable)
             except AnsibleUndefinedVariable as e:
-                raise AnsibleUndefinedVariable("%s: %s" % (to_native(variable), e.message))
+                # Instead of failing here prematurely, return an Undefined
+                # object which fails only after its first usage allowing us to
+                # do lazy evaluation and passing it into filters/tests that
+                # operate on such objects.
+                return self._templar.environment.undefined(
+                    hint=f"{variable}: {e.message}",
+                    name=varname,
+                    exc=AnsibleUndefinedVariable,
+                )
             except Exception as e:
                 msg = getattr(e, 'message', None) or to_native(e)
                 raise AnsibleError("An unhandled exception occurred while templating '%s'. "
diff --git a/test/integration/targets/template/lazy_eval.yml b/test/integration/targets/template/lazy_eval.yml
new file mode 100644
index 00000000000..1acd36c7256
--- /dev/null
+++ b/test/integration/targets/template/lazy_eval.yml
@@ -0,0 +1,24 @@
+- hosts: testhost
+  gather_facts: false
+  vars:
+    deep_undefined: "{{ nested_undefined_variable }}"
+  tasks:
+    - name: These do not throw an error, deep_undefined is just evaluated to undefined, since 2.13
+      assert:
+        that:
+          - lazy_eval or deep_undefined
+          - deep_undefined is undefined
+          - deep_undefined|default('defaulted') == 'defaulted'
+      vars:
+        lazy_eval: true
+
+    - name: EXPECTED FAILURE actually using deep_undefined fails
+      debug:
+        msg: "{{ deep_undefined }}"
+      ignore_errors: true
+      register: res
+
+    - assert:
+        that:
+          - res.failed
+          - res.msg is contains("'nested_undefined_variable' is undefined")
diff --git a/test/integration/targets/template/runme.sh b/test/integration/targets/template/runme.sh
index 78f8d7b5fb8..14cfaf992bd 100755
--- a/test/integration/targets/template/runme.sh
+++ b/test/integration/targets/template/runme.sh
@@ -40,3 +40,5 @@ ansible-playbook unsafe.yml -v "$@"
 
 # ensure Jinja2 overrides from a template are used
 ansible-playbook in_template_overrides.yml -v "$@"
+
+ansible-playbook lazy_eval.yml -i ../../inventory -v "$@"
diff --git a/test/units/playbook/test_conditional.py b/test/units/playbook/test_conditional.py
index 17284ca2258..8729ba9e4b3 100644
--- a/test/units/playbook/test_conditional.py
+++ b/test/units/playbook/test_conditional.py
@@ -121,19 +121,6 @@ class TestConditional(unittest.TestCase):
                                self._eval_con,
                                when, variables)
 
-    def test_dict_undefined_values_is_defined(self):
-        variables = {'dict_value': 1,
-                     'some_defined_dict_with_undefined_values': {'key1': 'value1',
-                                                                 'key2': '{{ dict_value }}',
-                                                                 'key3': '{{ undefined_dict_value }}'
-                                                                 }}
-
-        when = [u"some_defined_dict_with_undefined_values is defined"]
-        self.assertRaisesRegex(errors.AnsibleError,
-                               "The conditional check 'some_defined_dict_with_undefined_values is defined' failed.",
-                               self._eval_con,
-                               when, variables)
-
     def test_is_defined(self):
         variables = {'some_defined_thing': True}
         when = [u"some_defined_thing is defined"]