diff --git a/labelbox/schema/data_row_metadata.py b/labelbox/schema/data_row_metadata.py
index 47242e10b..666e88a16 100644
--- a/labelbox/schema/data_row_metadata.py
+++ b/labelbox/schema/data_row_metadata.py
@@ -158,7 +158,7 @@ def _lookup_in_index_by_name(reserved_index, custom_index, name):
         elif name in custom_index:
             return custom_index[name]
         else:
-            raise KeyError(f"There is no metadata with name {name}")
+            raise KeyError(f"There is no metadata with name '{name}'")
 
     def get_by_name(
         self, name: str
@@ -528,8 +528,8 @@ def _batch_upsert(
                     data_row_id=m.data_row_id,
                     fields=list(
                         chain.from_iterable(
-                            self._parse_upsert(m) for m in m.fields))).dict(
-                                by_alias=True))
+                            self._parse_upsert(f, m.data_row_id)
+                            for f in m.fields))).dict(by_alias=True))
         res = _batch_operations(_batch_upsert, items, self._batch_size)
         return res
 
@@ -689,8 +689,12 @@ def _upsert_schema(
     def _load_option_by_name(self, metadatum: DataRowMetadataField):
         is_value_a_valid_schema_id = metadatum.value in self.fields_by_id
         if not is_value_a_valid_schema_id:
-            metadatum.value = self.get_by_name(
-                metadatum.name)[metadatum.value].uid
+            metadatum_by_name = self.get_by_name(metadatum.name)
+            if metadatum.value not in metadatum_by_name:
+                raise KeyError(
+                    f"There is no enum option by name '{metadatum.value}' for enum name '{metadatum.name}'"
+                )
+            metadatum.value = metadatum_by_name[metadatum.value].uid
 
     def _load_schema_id_by_name(self, metadatum: DataRowMetadataField):
         """
@@ -706,7 +710,9 @@ def _load_schema_id_by_name(self, metadatum: DataRowMetadataField):
                 self._load_option_by_name(metadatum)
 
     def _parse_upsert(
-            self, metadatum: DataRowMetadataField
+            self,
+            metadatum: DataRowMetadataField,
+            data_row_id: Optional[str] = None
     ) -> List[_UpsertDataRowMetadataInput]:
         """Format for metadata upserts to GQL"""
 
@@ -720,21 +726,27 @@ def _parse_upsert(
                     f"Schema Id `{metadatum.schema_id}` not found in ontology")
 
         schema = self.fields_by_id[metadatum.schema_id]
-
-        if schema.kind == DataRowMetadataKind.datetime:
-            parsed = _validate_parse_datetime(metadatum)
-        elif schema.kind == DataRowMetadataKind.string:
-            parsed = _validate_parse_text(metadatum)
-        elif schema.kind == DataRowMetadataKind.number:
-            parsed = _validate_parse_number(metadatum)
-        elif schema.kind == DataRowMetadataKind.embedding:
-            parsed = _validate_parse_embedding(metadatum)
-        elif schema.kind == DataRowMetadataKind.enum:
-            parsed = _validate_enum_parse(schema, metadatum)
-        elif schema.kind == DataRowMetadataKind.option:
-            raise ValueError("An Option id should not be set as the Schema id")
-        else:
-            raise ValueError(f"Unknown type: {schema}")
+        try:
+            if schema.kind == DataRowMetadataKind.datetime:
+                parsed = _validate_parse_datetime(metadatum)
+            elif schema.kind == DataRowMetadataKind.string:
+                parsed = _validate_parse_text(metadatum)
+            elif schema.kind == DataRowMetadataKind.number:
+                parsed = _validate_parse_number(metadatum)
+            elif schema.kind == DataRowMetadataKind.embedding:
+                parsed = _validate_parse_embedding(metadatum)
+            elif schema.kind == DataRowMetadataKind.enum:
+                parsed = _validate_enum_parse(schema, metadatum)
+            elif schema.kind == DataRowMetadataKind.option:
+                raise ValueError(
+                    "An Option id should not be set as the Schema id")
+            else:
+                raise ValueError(f"Unknown type: {schema}")
+        except ValueError as e:
+            error_str = f"Could not validate metadata [{metadatum}]"
+            if data_row_id:
+                error_str += f", data_row_id='{data_row_id}'"
+            raise ValueError(f"{error_str}. Reason: {e}")
 
         return [_UpsertDataRowMetadataInput(**p) for p in parsed]
 
@@ -824,7 +836,7 @@ def _validate_parse_datetime(
         field.value = datetime.fromisoformat(field.value)
     elif not isinstance(field.value, datetime):
         raise TypeError(
-            f"value for datetime fields must be either a string or datetime object. Found {type(field.value)}"
+            f"Value for datetime fields must be either a string or datetime object. Found {type(field.value)}"
         )
 
     return [{
@@ -842,7 +854,7 @@ def _validate_parse_text(
 
     if len(field.value) > String.max_length:
         raise ValueError(
-            f"string fields cannot exceed {String.max_length} characters.")
+            f"String fields cannot exceed {String.max_length} characters.")
 
     return [field.dict(by_alias=True)]