diff --git a/datalab/datalab_session/tests/test_operations.py b/datalab/datalab_session/tests/test_operations.py
index 2743de1..f540a42 100644
--- a/datalab/datalab_session/tests/test_operations.py
+++ b/datalab/datalab_session/tests/test_operations.py
@@ -177,9 +177,9 @@ def test_operate(self, mock_create_jpgs, mock_save_fits_and_thumbnails, mock_get
         # return the test fits paths in order of the input_files instead of aws fetch
         mock_get_fits.side_effect = [self.test_fits_1_path, self.test_fits_2_path]
         # save temp output to a known path so we can test it
-        mock_named_tempfile.return_value.name = self.temp_median_path
+        mock_named_tempfile.return_value.__enter__.return_value.name = self.temp_median_path
         # avoids overwriting our output
-        mock_create_jpgs.return_value = ('test_path', 'test_path')
+        mock_create_jpgs.return_value.__enter__.return_value = ('test_path', 'test_path')
         # don't save to s3
         mock_save_fits_and_thumbnails.return_value = self.temp_median_path
 
@@ -230,9 +230,9 @@ def test_operate(self, mock_get_fits, mock_named_tempfile, mock_create_jpgs, moc
         # return the test fits paths in order of the input_files instead of aws fetch
         mock_get_fits.side_effect = [self.test_red_path, self.test_green_path, self.test_blue_path]
         # save temp output to a known path so we can test
-        mock_named_tempfile.return_value.name = self.temp_rgb_path
+        mock_named_tempfile.return_value.__enter__.return_value.name = self.temp_rgb_path
         # avoids overwriting our output
-        mock_create_jpgs.return_value = ('test_path', 'test_path')
+        mock_create_jpgs.return_value.__enter__.return_value = ('test_path', 'test_path')
         # don't save to s3
         mock_save_fits_and_thumbnails.return_value = self.temp_rgb_path
 
@@ -300,9 +300,9 @@ def test_operate(self, mock_create_jpgs, mock_save_fits_and_thumbnails, mock_get
         mock_get_fits.side_effect = [self.test_fits_1_path, self.test_fits_2_path,
                                      self.temp_fits_1_negative_path, self.temp_fits_2_negative_path]
         # save temp output to a known path so we can test it
-        mock_named_tempfile.return_value.name = self.temp_stacked_path
+        mock_named_tempfile.return_value.__enter__.return_value.name = self.temp_stacked_path
         # avoids overwriting our output
-        mock_create_jpgs.return_value = ('test_path', 'test_path')
+        mock_create_jpgs.return_value.__enter__.return_value = ('test_path', 'test_path')
         # don't save to s3
         mock_save_fits_and_thumbnails.return_value = self.temp_stacked_path
 
diff --git a/datalab/datalab_session/utils/file_utils.py b/datalab/datalab_session/utils/file_utils.py
index 27ec07a..00c3392 100644
--- a/datalab/datalab_session/utils/file_utils.py
+++ b/datalab/datalab_session/utils/file_utils.py
@@ -95,8 +95,11 @@ def create_jpgs(cache_key, fits_paths: str, color=False, zmin=None, zmax=None) -
     try:
       yield large_jpg_path, thumbnail_jpg_path
     finally:
-      os.remove(large_jpg_path)
-      os.remove(thumbnail_jpg_path)
+      try:
+        os.remove(large_jpg_path)
+        os.remove(thumbnail_jpg_path)
+      except FileNotFoundError:
+        pass
 
 def crop_arrays(array_list: list):
   """