The _ssl module has failed building (on 3.4) on OS X Tiger for a long time:
http://buildbot.python.org/all/builders/x86%20Tiger%203.x/builds/6075/steps/test/logs/stdio

Given the error messages, and given how old OS X Tiger is (according to Google, the system OpenSSL is 0.9.7), I'm inclined to think it is because of missing features on the system OpenSSL.

Is there any point in supporting OS X Tiger in 3.4? Should the _ssl module be updated to use conditionals for "new" (i.e. < 7 years old) OpenSSL features?

New changeset 02f9335b7efb by Antoine Pitrou in branch 'default':
Issue #17581: try to fix building on old OpenSSL versions
http://hg.python.org/cpython/rev/02f9335b7efb

New changeset ad9effdc0ac3 by Antoine Pitrou in branch 'default':
Further compiling fixes (issue #17581)
http://hg.python.org/cpython/rev/ad9effdc0ac3

Ok, some of the features here are relatively new (they are only 3 years old), so it makes sense to conditionally enable them. The question remains of whether Tiger is an useful target to support, though.

This is fixed. I'll let other people settle the support issue.

Thanks for fixing the break.  As time goes on, active support of 10.4 Tiger becomes less important but having the buildbot there is an inexpensive way to test backward compatibility, issues that might also arise on other platforms.  For 2.7.x and 3.2.x, we still produce 32-bit binary installers that support 10.3 and later systems.  For 3.3.x, the released 32-bit binary installer support now only supports 10.5 and later.  However, the daily DMG building still produces the 10.3 variant for 3.3 and I still occasionally build and test those variants.  I know there are still some users of these older systems out there as I see bug reports about them to other projects (e.g. MacPorts).  If we reach a point where it becomes more difficult to fully support 10.4, we can revisit the question.