diff --git a/deckhand/engine/layering.py b/deckhand/engine/layering.py
index fed632fb..ed3c521c 100644
--- a/deckhand/engine/layering.py
+++ b/deckhand/engine/layering.py
@@ -405,9 +405,11 @@ class DocumentLayering(object):
                                                   action_path)
                 if from_child is None:
                     raise errors.MissingDocumentKey(
-                        child=child_data.data,
-                        parent=overall_data.data,
-                        key=action_path)
+                        child_schema=child_data.schema,
+                        child_name=child_data.name,
+                        parent_schema=overall_data.schema,
+                        parent_name=overall_data.name,
+                        action=action)
 
                 engine_utils.deep_delete(from_child, overall_data.data, None)
 
@@ -417,9 +419,11 @@ class DocumentLayering(object):
 
             if from_child is None:
                 raise errors.MissingDocumentKey(
-                    child=child_data.data,
-                    parent=overall_data.data,
-                    key=action_path)
+                    child_schema=child_data.schema,
+                    child_name=child_data.name,
+                    parent_schema=overall_data.schema,
+                    parent_name=overall_data.name,
+                    action=action)
 
             if (isinstance(from_parent, dict)
                     and isinstance(from_child, dict)):
@@ -436,9 +440,11 @@ class DocumentLayering(object):
 
             if from_child is None:
                 raise errors.MissingDocumentKey(
-                    child=child_data.data,
-                    parent=overall_data.data,
-                    key=action_path)
+                    child_schema=child_data.schema,
+                    child_name=child_data.name,
+                    parent_schema=overall_data.schema,
+                    parent_name=overall_data.name,
+                    action=action)
 
             overall_data.data = utils.jsonpath_replace(
                 overall_data.data, from_child, action_path)
diff --git a/deckhand/errors.py b/deckhand/errors.py
index 80631bd9..6c820fc4 100644
--- a/deckhand/errors.py
+++ b/deckhand/errors.py
@@ -230,12 +230,22 @@ class SubstitutionDependencyCycle(DeckhandException):
 
 
 class MissingDocumentKey(DeckhandException):
-    """The key does not exist in the "rendered_data".
+    """Either the parent or child document data is missing the action path
+    used for layering.
 
     **Troubleshoot:**
+
+    * Check that the action path exists in the data section for both child
+      and parent documents being layered together.
+    * Note that previous delete layering actions can affect future layering
+      actions by removing a path needed by a future layering action.
+    * Note that substitutions that substitute in lists or objects into the
+      rendered data for a document can also complicate debugging this issue.
     """
-    msg_fmt = ("Missing document key %(key)s from either parent or child. "
-               "Parent: %(parent)s. Child: %(child)s.")
+    msg_fmt = ("Missing action path in %(action)s needed for layering from "
+               "either the data section of the parent [%(parent_schema)s] "
+               "%(parent_name)s or child [%(child_schema)s] %(child_name)s "
+               "document.")
     code = 400