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test_startfile uses a weak time.sleep(0.1) to wait until the process started by os.startfile() completes. Instead of a sleep, can't support.rmtree() retry on "WindowsError: [Error 32] The process cannot access the file because it is being used by another process" error? For example, retry every 100 ms during 10 seconds?
It's easy to reproduce the bug on Python 2.7: just remove the time.sleep() call in tests.
http://buildbot.python.org/all/builders/x86%20Windows7%202.7/builds/145/steps/test/logs/stdio
0:23:42 [363/402/1] test_startfile crashed
[1, 5.638000011444092]
Traceback (most recent call last):
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\runpy.py", line 174, in _run_module_as_main
 "__main__", fname, loader, pkg_name)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\runpy.py", line 72, in _run_code
 exec code in run_globals
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\regrtest.py", line 1877, in <module>
 main_in_temp_cwd()
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\regrtest.py", line 1864, in main_in_temp_cwd
 main()
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\contextlib.py", line 35, in __exit__
 self.gen.throw(type, value, traceback)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 769, in temp_cwd
 rmtree(name)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 293, in rmtree
 _rmtree(path)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 249, in _rmtree
 _waitfor(lambda p: _force_run(p, os.rmdir, p), path)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 202, in _waitfor
 func(pathname)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 249, in <lambda>
 _waitfor(lambda p: _force_run(p, os.rmdir, p), path)
 File "D:\cygwin\home\db3l\buildarea2円.7.bolen-windows7\build\lib\test\support\__init__.py", line 197, in _force_run
 return func(*args)
WindowsError: [Error 32] The process cannot access the file because it is being used by another process: 'D:\\cygwin\\home\\db3l\\buildarea\2円.7.bolen-windows7\\build\\build\\test_python_2944'
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If it's too complex to implement a retry (too complex? really?), an obvious hack is to increase the sleep in test_startfile.py from 100 ms to 200 ms...