diff --git a/changelogs/fragments/fix_errors.yml b/changelogs/fragments/fix_errors.yml
new file mode 100644
index 00000000000..995cc28ffda
--- /dev/null
+++ b/changelogs/fragments/fix_errors.yml
@@ -0,0 +1,2 @@
+bugfixes:
+  - Errors now preserve stacked error messages even when YAML is involved.
diff --git a/lib/ansible/errors/__init__.py b/lib/ansible/errors/__init__.py
index f003b589c8a..78853757f8a 100644
--- a/lib/ansible/errors/__init__.py
+++ b/lib/ansible/errors/__init__.py
@@ -66,14 +66,18 @@ class AnsibleError(Exception):
         from ansible.parsing.yaml.objects import AnsibleBaseYAMLObject
 
         message = [self._message]
+
+        # Add from previous exceptions
+        if self.orig_exc:
+            message.append('. %s' % to_native(self.orig_exc))
+
+        # Add from yaml to give specific file/line no
         if isinstance(self.obj, AnsibleBaseYAMLObject):
             extended_error = self._get_extended_error()
             if extended_error and not self._suppress_extended_error:
                 message.append(
                     '\n\n%s' % to_native(extended_error)
                 )
-        elif self.orig_exc:
-            message.append('. %s' % to_native(self.orig_exc))
 
         return ''.join(message)
 
diff --git a/lib/ansible/playbook/base.py b/lib/ansible/playbook/base.py
index f93fb5ef5f9..46483efda2d 100644
--- a/lib/ansible/playbook/base.py
+++ b/lib/ansible/playbook/base.py
@@ -19,7 +19,7 @@ from ansible import context
 from ansible.errors import AnsibleError, AnsibleParserError, AnsibleUndefinedVariable, AnsibleAssertionError
 from ansible.module_utils.six import string_types
 from ansible.module_utils.parsing.convert_bool import boolean
-from ansible.module_utils.common.text.converters import to_text, to_native
+from ansible.module_utils.common.text.converters import to_text
 from ansible.parsing.dataloader import DataLoader
 from ansible.playbook.attribute import Attribute, FieldAttribute, ConnectionFieldAttribute, NonInheritableFieldAttribute
 from ansible.plugins.loader import module_loader, action_loader
@@ -567,14 +567,14 @@ class FieldAttributeBase:
                 setattr(self, name, value)
             except (TypeError, ValueError) as e:
                 value = getattr(self, name)
-                raise AnsibleParserError("the field '%s' has an invalid value (%s), and could not be converted to %s. "
-                                         "The error was: %s" % (name, value, attribute.isa, e), obj=self.get_ds(), orig_exc=e)
+                raise AnsibleParserError(f"the field '{name}' has an invalid value ({value!r}), and could not be converted to {attribute.isa}.",
+                                         obj=self.get_ds(), orig_exc=e)
             except (AnsibleUndefinedVariable, UndefinedError) as e:
                 if templar._fail_on_undefined_errors and name != 'name':
                     if name == 'args':
-                        msg = "The task includes an option with an undefined variable. The error was: %s" % (to_native(e))
+                        msg = "The task includes an option with an undefined variable."
                     else:
-                        msg = "The field '%s' has an invalid value, which includes an undefined variable. The error was: %s" % (name, to_native(e))
+                        msg = f"The field '{name}' has an invalid value, which includes an undefined variable."
                     raise AnsibleParserError(msg, obj=self.get_ds(), orig_exc=e)
 
         self._finalized = True
diff --git a/test/integration/targets/template/tasks/main.yml b/test/integration/targets/template/tasks/main.yml
index d96941fd32d..8a45494033f 100644
--- a/test/integration/targets/template/tasks/main.yml
+++ b/test/integration/targets/template/tasks/main.yml
@@ -714,7 +714,9 @@
 
 - name: check that proper error message is emitted when in operator is used
   assert:
-    that: "\"The error was: 'y' is undefined\n\n\" in error.msg"
+    that:
+      - '"The task includes an option with an undefined variable" in error.msg'
+      - "\"'y' is undefined\n\n\" in error.msg"
 
 - template:
     src: template_import_macro_globals.j2