diff --git a/spiffworkflow-backend/src/spiffworkflow_backend/services/process_instance_service.py b/spiffworkflow-backend/src/spiffworkflow_backend/services/process_instance_service.py
index ed2ea918f..37f77ac14 100644
--- a/spiffworkflow-backend/src/spiffworkflow_backend/services/process_instance_service.py
+++ b/spiffworkflow-backend/src/spiffworkflow_backend/services/process_instance_service.py
@@ -278,6 +278,9 @@ class ProcessInstanceService:
                 for list_index, list_value in enumerate(value):
                     if isinstance(list_value, str):
                         yield (identifier, list_value, list_index)
+                    if isinstance(list_value, dict) and len(list_value) == 1:
+                        for v in list_value.values():
+                            yield (identifier, v, list_index)
 
     @classmethod
     def file_data_models_for_data(
@@ -308,7 +311,11 @@ class ProcessInstanceService:
             if model.list_index is None:
                 data[model.identifier] = digest_reference
             else:
-                data[model.identifier][model.list_index] = digest_reference
+                old_value = data[model.identifier][model.list_index]
+                new_value: Any = digest_reference
+                if isinstance(old_value, dict) and len(old_value) == 1:
+                    new_value = {k: digest_reference for k in old_value.keys()}
+                data[model.identifier][model.list_index] = new_value
 
     @classmethod
     def save_file_data_and_replace_with_digest_references(
diff --git a/spiffworkflow-backend/tests/spiffworkflow_backend/unit/test_process_instance_service.py b/spiffworkflow-backend/tests/spiffworkflow_backend/unit/test_process_instance_service.py
index 436810cca..0c27a5383 100644
--- a/spiffworkflow-backend/tests/spiffworkflow_backend/unit/test_process_instance_service.py
+++ b/spiffworkflow-backend/tests/spiffworkflow_backend/unit/test_process_instance_service.py
@@ -89,7 +89,7 @@ class TestProcessInstanceService(BaseTest):
         self._check_sample_file_data_model("uploaded_files", 0, models[0])
         self._check_sample_file_data_model("uploaded_files", 1, models[1])
 
-    def test_can_create_file_data_models_for_fix_of_file_data_and_non_file_data_values(
+    def test_can_create_file_data_models_for_mix_of_file_data_and_non_file_data_values(
         self,
         app: Flask,
         with_db_and_bpmn_file_cleanup: None,
@@ -122,6 +122,8 @@ class TestProcessInstanceService(BaseTest):
     ) -> None:
         data = {
             "not_a_file": "just a value",
+            "also_no_files": ["not a file", "also not a file"],
+            "still_no_files": [{"key": "value"}],
         }
         models = ProcessInstanceService.file_data_models_for_data(data, 111)
 
@@ -189,3 +191,25 @@ class TestProcessInstanceService(BaseTest):
             ],
             "not_a_file3": "just a value3",
         }
+
+    def test_can_create_file_data_models_for_mulitple_single_file_data_values(
+        self,
+        app: Flask,
+        with_db_and_bpmn_file_cleanup: None,
+        with_super_admin_user: UserModel,
+    ) -> None:
+        data = {
+            "File": [
+                {
+                    "supporting_files": self.SAMPLE_FILE_DATA,
+                },
+                {
+                    "supporting_files": self.SAMPLE_FILE_DATA,
+                },
+            ],
+        }
+        models = ProcessInstanceService.file_data_models_for_data(data, 111)
+
+        assert len(models) == 2
+        self._check_sample_file_data_model("File", 0, models[0])
+        self._check_sample_file_data_model("File", 1, models[1])