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Simpletest's drupal_web_test_case.php sets a value for the "file_private_path" directory. testPrivateFileTransfer() test in file.test tries to do a GET of a created private file. If the site's settings.php file is assigning a custom value to "file_private_path", that's where the GET will look - not in the directory set up by simpletest - so the GET will fail.
I don't know what to do about this, maybe only add a warning to the test to comment out those settings while testing?
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