diff --git a/Lib/packaging/tests/test_pypi_server.py b/Lib/packaging/tests/test_pypi_server.py
--- a/Lib/packaging/tests/test_pypi_server.py
+++ b/Lib/packaging/tests/test_pypi_server.py
@@ -67,6 +67,9 @@
             # now try serving a content that do exists
             self.assertTrue(uses_local_files_for(server, "/simple/index.html"))
 
+            # test it works when reading twice the same resource
+            self.assertTrue(uses_local_files_for(server, "/simple/index.html"))
+
             # and another one in another root path
             self.assertTrue(uses_local_files_for(server, "/external/index.html"))