diff --git a/cli/onionshare_cli/web/send_base_mode.py b/cli/onionshare_cli/web/send_base_mode.py
index e608298b..2e906081 100644
--- a/cli/onionshare_cli/web/send_base_mode.py
+++ b/cli/onionshare_cli/web/send_base_mode.py
@@ -44,8 +44,9 @@ class SendBaseModeWeb:
         self.download_filesize = None
         self.zip_writer = None
 
-        # Store the tempfile objects here, so when they're garbage collected the files are deleted
-        self.gzip_files = []
+        # Create a temporary dir to store gzip files in
+        self.gzip_tmp_dir = tempfile.TemporaryDirectory(dir=self.common.build_tmp_dir())
+        self.gzip_counter = 0
 
         # If autostop_sharing, only allow one download at a time
         self.download_in_progress = False
@@ -193,15 +194,15 @@ class SendBaseModeWeb:
         # gzip compress the individual file, if it hasn't already been compressed
         if use_gzip:
             if filesystem_path not in self.gzip_individual_files:
-                self.gzip_files.append(
-                    tempfile.NamedTemporaryFile("wb+", dir=self.common.build_tmp_dir())
+                gzip_filename = os.path.join(
+                    self.gzip_tmp_dir.name, str(self.gzip_counter)
                 )
-                gzip_file = self.gzip_files[-1]
-                self._gzip_compress(filesystem_path, gzip_file.name, 6, None)
-                self.gzip_individual_files[filesystem_path] = gzip_file.name
+                self.gzip_counter += 1
+                self._gzip_compress(filesystem_path, gzip_filename, 6, None)
+                self.gzip_individual_files[filesystem_path] = gzip_filename
 
                 # Cleanup this temp file
-                self.web.cleanup_tempfiles.append(gzip_file)
+                self.web.cleanup_tempfiles.append(gzip_filename)
 
             file_to_download = self.gzip_individual_files[filesystem_path]
             filesize = os.path.getsize(self.gzip_individual_files[filesystem_path])