diff --git a/deckhand/engine/document_validation.py b/deckhand/engine/document_validation.py
index 70e5abac..68f8a978 100644
--- a/deckhand/engine/document_validation.py
+++ b/deckhand/engine/document_validation.py
@@ -240,14 +240,18 @@ class DataSchemaValidator(GenericValidator):
         parent_path_to_error_in_document = '.'.join(
             path_to_error_in_document.split('.')[:-1]) or '.'
         try:
-            # NOTE(fmontei): Because validation is performed on fully rendered
-            # documents, it is necessary to omit the parts of the data section
-            # where substitution may have occurred to avoid exposing any
-            # secrets. While this may make debugging a few validation failures
-            # more difficult, it is a necessary evil.
+            # NOTE(felipemonteiro): Because validation is performed on fully
+            # rendered documents, it is necessary to omit the parts of the data
+            # section where substitution may have occurred to avoid exposing
+            # any secrets. While this may make debugging a few validation
+            # failures more difficult, it is a necessary evil.
             sanitized_document = (
                 SecretsSubstitution.sanitize_potential_secrets(
                     error, document))
+            # This incurs some degree of overhead as caching here won't make
+            # a big difference as we are not parsing commonly referenced
+            # JSON paths -- but this branch is only hit during error handling
+            # so this should be OK.
             parent_error_section = utils.jsonpath_parse(
                 sanitized_document, parent_path_to_error_in_document)
         except Exception:
diff --git a/deckhand/errors.py b/deckhand/errors.py
index 5918d3b5..c5303d57 100644
--- a/deckhand/errors.py
+++ b/deckhand/errors.py
@@ -12,11 +12,12 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-import yaml
+import collections
 
 import falcon
 from oslo_log import log as logging
 import six
+import yaml
 
 LOG = logging.getLogger(__name__)
 
@@ -29,6 +30,34 @@ def get_version_from_request(req):
     return 'N/A'
 
 
+def _safe_yaml_dump(error_response):
+    """Cast every instance of ``DocumentDict`` into a dictionary for
+    compatibility with ``yaml.safe_dump``.
+
+    This should only be called for error formatting.
+    """
+    is_dict_sublcass = (
+        lambda v: type(v) is not dict and issubclass(v.__class__, dict)
+    )
+
+    def _to_dict(value, parent):
+        if isinstance(value, (list, tuple, set)):
+            for v in value:
+                _to_dict(v, value)
+        elif isinstance(value, collections.Mapping):
+            for v in value.values():
+                _to_dict(v, value)
+        else:
+            if isinstance(parent, (list, tuple, set)):
+                parent[parent.index(value)] = (
+                    dict(value) if is_dict_sublcass(value) else value)
+            elif isinstance(parent, dict):
+                for k, v in parent.items():
+                    parent[k] = dict(v) if is_dict_sublcass(v) else v
+    _to_dict(error_response, None)
+    return yaml.safe_dump(error_response)
+
+
 def format_error_resp(req,
                       resp,
                       status_code=falcon.HTTP_500,
@@ -102,8 +131,7 @@ def format_error_resp(req,
         'retry': True if status_code is falcon.HTTP_500 else False
     }
 
-    # Don't use yaml.safe_dump to handle unicode correctly.
-    resp.body = yaml.dump(error_response)
+    resp.body = _safe_yaml_dump(error_response)
     resp.status = status_code