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While building python from source on a MacOS, I accidntally overwrote the python that came with MacOS, now it doesn't have SSL. I tried to build again by running --with-ssl option

./configure --with-ssl

but when I subsequently ran make, it said this

Python build finished, but the necessary bits to build these modules were not found: _bsddb _ssl dl imageop linuxaudiodev ossaudiodev readline spwd sunaudiodev To find the necessary bits, look in setup.py in detect_modules() for the module's name.

It's not clear to me from looking at setup.py what I'm supposed to do to find the "necessary bits". What can I do to build python with SSL on MacOS?

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First of all, MacOS only includes LibreSSL 2.2.7 libraries and no headers, you really want to install OpenSSL using homebrew:

$ brew install openssl

The openssl formula is a keg-only formula because the LibreSSL library is shadowing OpenSSL and Homebrew will not interfere with this. This means that you can find OpenSSL not in /usr/local but in /usr/local/opt/openssl. But Homebrew includes the necessary command-line tools to figure out what path to use.

You then need to tell configure about these. If you are building Python 3.7 or newer, use the --with-openssl switch:

./configure --with-openssl=$(brew --prefix openssl)

If you are building an older release, set the CPPFLAGS and LDFLAGS environment variables:

CPPFLAGS="-I$(brew --prefix openssl)/include" \ LDFLAGS="-L$(brew --prefix openssl)/lib" \ ./configure

and the Python configuration infrastructure takes it from there.

Know that now ancient Python releases (2.6 or older, 3.0-3.4) only work with OpenSSL 1.0.x and before, which no longer is installable from homebrew core.

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2022 update: you have a choice between OpenSSL 1.1.1 and 3.0 (both work on recent CPython versions). In brew commands you might have to specify [email protected] or openssl@3 (e.g. brew install [email protected] and brew --prefix [email protected]). As of Python 3.11.0, OpenSSL 1.1.1 is often the default, so you might prefer that right now. But that might change soon.
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Just open setup.py and find method detect_modules(). It has some lines like (2.7.11 for me):

 # Detect SSL support for the socket module (via _ssl) search_for_ssl_incs_in = [ '/usr/local/ssl/include', '/usr/contrib/ssl/include/' ] ssl_incs = find_file('openssl/ssl.h', inc_dirs, search_for_ssl_incs_in ) if ssl_incs is not None: krb5_h = find_file('krb5.h', inc_dirs, ['/usr/kerberos/include']) if krb5_h: ssl_incs += krb5_h ssl_libs = find_library_file(self.compiler, 'ssl',lib_dirs, ['/usr/local/ssl/lib', '/usr/contrib/ssl/lib/' ] ) if (ssl_incs is not None and ssl_libs is not None): exts.append( Extension('_ssl', ['_ssl.c'], include_dirs = ssl_incs, library_dirs = ssl_libs, libraries = ['ssl', 'crypto'], depends = ['socketmodule.h']), ) else: missing.append('_ssl')

So it seems that you need SSL and Kerberos. Kerberos comes installed with Mac. So You need to install openssl. You can do it with brew:

brew install openssl

openssl headers could be installed in a path different than Python will search. So issue

locate ssl.h

and add the path to search_for_ssl_incs_in. For example for me it is:

/usr/local/Cellar/openssl/1.0.2d_1/include/openssl/ssl.h

So I should add /usr/local/Cellar/openssl/1.0.2d_1/include/ to search_for_ssl_incs_in.

Don't forget that these are for Python 2.7.11. But the process should be same.

Hope that helps.

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I changed the paths to /opt/local/... for the MacPorts OpenSSL. The built succeeded, but Python failed to import the _ssl module due to undefined symbols. Installing OpenSSL from source solved the problem, using the default paths in CPython's setup.py.
I had the same problem but was able to get it working with openSSL from Homebrew. Here's how stackoverflow.com/a/46476640/2934226
There is absolutely no need to edit setup.py. Just make sure to set the CPPFLAGS and LDFLAGS variables when running configure: CPPFLAGS="-I$(brew --prefix openssl)/include" LDFLAGS="-L$(brew --prefix openssl)/lib" ./configure

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