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The Refleaks 2.7 job hangs on "AMD64 Windows8.1 Refleaks 2.7" and "x86 Gentoo Refleaks 2.7" buildbots.
(1) Gentoo
http://buildbot.python.org/all/builders/x86%20Gentoo%20Refleaks%202.7/builds/21
StartSat Jun 3 00:00:00 2017
Elapsed328 hrs, 17 mins, 37 secs
http://buildbot.python.org/all/builders/x86%20Gentoo%20Refleaks%202.7/builds/21/steps/test/logs/stdio
...
running: test_io (1177378 sec)
running: test_io (1177408 sec)
running: test_io (1177438 sec)
running: test_io (1177468 sec)
(2) Windows
http://buildbot.python.org/all/builders/AMD64%20Windows8.1%20Refleaks%202.7/builds/27
Elasped: 88 hrs, 11 mins, 5 secs
http://buildbot.python.org/all/builders/AMD64%20Windows8.1%20Refleaks%202.7/builds/27/steps/test/logs/stdio
...
running: test_regrtest (304919 sec)
running: test_regrtest (304949 sec)
running: test_regrtest (304979 sec)
running: test_regrtest (305009 sec)
running: test_regrtest (305039 sec)
running: test_regrtest (305069 sec)

Oh, for test_regrtest which hangs on Windows, I'm quite sure that it comes from test_crashed() which opens a popup!
In the master branch, test_crashed() uses faulthandler._sigsegv() which disables the Windows popup using SetErrorMode() and _set_abort_behavior().
In Python 2.7, test_crashed() just calls ctypes.string_at(0) which doesn't prevent the Windows popup.
My PR https://github.com/python/cpython/pull/2423 implements support.SuppressCrashReport on Windows and so will allow to fix this issue!

New changeset 2d775589d98959abb9833121bd9d417003de56c0 by Victor Stinner in branch '2.7':
bpo-30705: Fix test_regrtest.test_crashed() (#2439)
https://github.com/python/cpython/commit/2d775589d98959abb9833121bd9d417003de56c0

It seems like "x86 Gentoo Refleaks 2.7" was fixed, I don't know how, but I don't care as soon as it works :-)
My commit 2d775589d98959abb9833121bd9d417003de56c0 fixed "./python -m test -R 3:3 test_regrtest" on Windows. I tested manually.
I consider that the bugs are now fixed. (If the bug is not really fixed, I will just reopen the bug.)