To follow up, Ned diagnosed this for me off-list. The cause was my recent upgrade to Mavericks, which causes the Xcode 5 command line tools to be installed differently. In case others have the same issue, the solution was to run:

xcode-select --install

(and accept the dialog box it pops up). This is a common issue with Mavericks and open-source projects (not just Python); Ned will add something to the README.

--Guido


On Tue, Feb 11, 2014 at 2:22 PM, Ned Deily <nad@acm.org> wrote:
In article
<CAP7+vJ+3sxE6LNt8QeHdni3-E4RwNTpqLVqNsGKLppCMWGA=yw@mail.gmail.com>,
 Guido van Rossum <guido@python.org> wrote:
> I don't happen to have OpenSSL configured on my OSX dev box right now. This
> usually leads to some warnings during the build stage and obviously various
> ssl-based tests don't work, but I can still get other stuff done.

As a side note, you shouldn't have to configure OpenSSL to build any of
the current branches of Python on OS X systems.  It should build
gracefully with the Apple-supplied headers and libssl/libcrypto, modulo
possible deprecation warnings in the recent releases of OS X.

--
 Ned Deily,
 nad@acm.org

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--
--Guido van Rossum (python.org/~guido)