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See http://bugs.python.org/issue30350#msg293663
http://buildbot.python.org/all/builders/AMD64%20Windows7%20SP1%20VS9.0%202.7/builds/83/steps/compile/logs/stdio
Build started: Project: _ssl, Configuration: Debug|x64
...
No Perl installation was found. Existing Makefiles are used.
...
IOError: [Errno 2] No such file or directory: 'crypto\\buildinf_amd64.h'

Perl should not be required - we should be checking these files in to our clone on svn.p.o for use when building. (Perl is only required by whoever creates the source tree, normally Zach.)
Perhaps it got missed in the latest update?

Perl is not required when using the PCbuild/ build files on any branch. It is currently required to use the PC/VS9.0 build files, at least for 64-bit builds, because I was not able to make it work (and not break the new system) in the time I had to get it done.

I don't really care if Jeremy installs Perl on the buildbot or if someone succeed to fix the dependency on the svn repository. I only care of seeing a green buildbot ;-)

The simple fix from my point of view is for Jeremy to install Perl :). But since he also mentioned having a patch ready in bpo-30350, I'd like to see it before declaring that installing Perl is what should be done.

Submitted PR-1805 that should restore perl-less building.
Also some open issues as noted in the PR.

I tried out PR1805 with Perl unavailable, and it seemed to build fine with `PC\VS9.0\build.bat -e -d -p x64`. However, trying `PC\VS9.0\amd64\python_d.exe -m test.ssltests` segfaults. Can you reproduce?

On my VM, ssltests pass, but both the Perl and non-Perl segfault in
test_ssl (and many others). My VM has just VS2008 installed, does
VS2010 come with an updated SDK?

OK, testing with the 7.1 SDK installed changes the crashes around, but something is really amiss. I'd like to do more testing, but it will need to wait until morning here.

Ok, sounds good. The two points you raised on the PR also sound fine, as far as I can tell.

Updated PR. It seems that in my testing back and forth, some build artifacts were affecting my outcomes. That's what I get for cutting corners...
Per Zach's comment, I've changed to VS project files to use the prepare_ssl.py include directories (include{suffix} vs inc{suffix}). This simplifies build_ssl.py further.
I have, however, left the "fix_buildinf()" code in place since it requires an update to the checked-in external OpenSSL before it can be removed.

Just a status check, as I would like to see my buildbot go green again. (This along with the PR on issue30339).

Any progress on this issue? The following buildbot still fails to build Python 2.7:
http://buildbot.python.org/all/builders/AMD64%20Windows7%20SP1%20VS9.0%202.7 

This is ready to be merged, pending any comments from Zach.

New changeset ebbccea997e03f60fec8308f2fb9e89a11521a74 by Victor Stinner (Jeremy Kloth) in branch '2.7':
bpo-30368: Update build_ssl.py to restore Perl-less building (#1805)
https://github.com/python/cpython/commit/ebbccea997e03f60fec8308f2fb9e89a11521a74

I checked AMD64 Windows7 SP1 VS9.0 2.7. Before the commit, the build 129 failed badly when building ssl:
http://buildbot.python.org/all/builders/AMD64%20Windows7%20SP1%20VS9.0%202.7/builds/129/steps/compile/logs/stdio
IOError: [Errno 2] No such file or directory: 'crypto\\buildinf_amd64.h'
In the first build with the commit, the compilation of ssl succeeded!
http://buildbot.python.org/all/builders/AMD64%20Windows7%20SP1%20VS9.0%202.7/builds/130
"_ssl - 0 error(s), 375 warning(s)"
... but the compilation step still failed, for other reasons. I see that 2 projects failed:
..\..\Modules\expat\xmlparse.c(13) : fatal error C1083: Cannot open include file: 'sys/time.h': No such file or directory
_elementtree - 1 error(s), 9 warning(s)
and
..\..\Modules\expat\xmlparse.c(13) : fatal error C1083: Cannot open include file: 'sys/time.h': No such file or directory
pyexpat - 1 error(s), 1 warning(s)
It may be related to the recent update of libexpat from 2.1.1 to 2.2.0?

In a previous build, build 111 (June 6), the compilation of _elementtree succeeded:
http://buildbot.python.org/all/builders/AMD64%20Windows7%20SP1%20VS9.0%202.7/builds/111/steps/compile/logs/stdio
_elementtree - 0 error(s), 10 warning(s)
I also see that the commit 0e4571a68a7f48e8469ef05b04ba3463d3fd82c0 which upgraded libexpat introduced "#ifdef WIN32". I see that libexpat 2.2.1, the new version, replace "#ifdef WIN32" with "#ifdef _WIN32". I tested manually and it seems to fix the compilation of xmlparse.c at least! So bpo-30694 which update expat from 2.2.0 to 2.2.1 should fix this buildbot.

So, I made final tests with the merged commit. I manually uninstalled (Active)Perl. Without the commit, the compilation of ssl failed on my Windows VM since I'm using VS 2008.
(1) using build.bat
git clean -fdx
In the VS2008 shell, type: PC\VS9.0\build.bat -e -d -p x64
=> you get a python_d.exe with a working _ssl module!
(2) using VS GUI
git clean -fdx
PCbuild\get_externals.bat
Open VS 2008, build the project
=> compilation of _ssl fails with a permission error about a temporay object file... I don't understand it
Rebuild the project
=> compilation of _ssl works, python_d.exe has a working _ssl module!
Except of the "temporary" (but reproductible) compilation error in the VS GUI, I confirm that the change fixes this issue!
I prefer to keep the issue open until the buildbot is repaired (expat issue).

Added PR to issue29591 to address issue building Expat. In short, the project files were not updated along with the copy of Expat.
I cannot reproduce the GUI build problem. I would need to see the build logs to attempt to resolve.

> Added PR to issue29591 to address issue building Expat. In short, the project files were not updated along with the copy of Expat.
I would prefer to first fix the new vulnerabilities, but upgrading expat to 2.2.1, and then review your change.
=> https://github.com/python/cpython/pull/2312 

Oh cool, with my commit 2ada64d2a073f85f135461833952dbe8d656810d "[2.7] bpo-30694: Upgrade Modules/expat/ to libexpat 2.2.1 (#2300)", and obvious Jeremy's previous fix!, the compile step of "AMD64 Windows7 SP1 VS9.0 2.7" succeeded for the first time since a long time!

The initial issue ("[2.7] OpenSSL compilation fails on AMD64 Windows7 SP1 VS9.0 2.7") is now fixed, so I close the issue. Thanks for the help everyone who helped me on this one!