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There is this kind of failures on Barry's new buildbot. It looks like warning messages should be ignored when checking gdb output:
======================================================================
FAIL: test_NULL_ob_type (test.test_gdb.PrettyPrintTests)
Ensure that a PyObject* with NULL ob_type is handled gracefully
----------------------------------------------------------------------
Traceback (most recent call last):
 File "/var/lib/buildbot/buildarea/3.x.warsaw-ubuntu-ppc/build/Lib/test/test_gdb.py", line 390, in test_NULL_ob_type
 'set v->ob_type=0')
 File "/var/lib/buildbot/buildarea/3.x.warsaw-ubuntu-ppc/build/Lib/test/test_gdb.py", line 361, in assertSane
 cmds_after_breakpoint=cmds_after_breakpoint)
 File "/var/lib/buildbot/buildarea/3.x.warsaw-ubuntu-ppc/build/Lib/test/test_gdb.py", line 150, in get_gdb_repr
 import_site=import_site)
 File "/var/lib/buildbot/buildarea/3.x.warsaw-ubuntu-ppc/build/Lib/test/test_gdb.py", line 132, in get_stack_trace
 self.assertEquals(err, '')
AssertionError: '\nwarning: not using untrusted file "/home/barry/.gdbinit"\n' != ''
- 
- warning: not using untrusted file "/home/barry/.gdbinit"
See http://www.python.org/dev/buildbot/builders/PPC%20Ubuntu%203.x/builds/0/steps/test/logs/stdio 

Seems to relate to this gdb feature:
http://sourceware.org/ml/gdb-patches/2005-05/msg00637.html
Barry: is your ~/.gdbinit world writable?
I can cook up a patch to ignore such warnings

Alternatively, it looks like having it owned by another user would do this.
For curiosity's sake, what's the output of:
 ls -al /home/barry/.gdbinit
on that buildbot?
Given that it's a security warning, should this simply be treated as misconfiguration, and be fixed on the buildbot?

It is a misconfiguration. I started my new buildbot with my environment active. I've since killed that and restarted it with a clean ~buildbot environment. So we shouldn't see this in my buildbots any more.
(FWIW, ~/.gdbinit is 644)

Closing "won't fix", since this was misconfiguration; filtering out such warnings might mask a security issue.