Ned Deily <n...@python.org> added the comment:

For Homebrew users, the Devguide currently recommends:

$ brew install openssl xz gdbm

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

I don't use Homebrew myself so I may be missing something
obvious but, after a bit of experimentation,
I think the following might be the simplest version of the
above that works with Homebrew installed in a non-default location:

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

Could you try it on your systems, please?

BTW, I notice that you are also installing zlib. There was a
longstanding bug in the 2.7 setup.py that caused the system
zlib to not be found in some cases. That was fixed some time
back. So there is no normally no need to install a third-party
zlib; current Python builds will automatically use the
Apple-supplied system zlib.

Since, like openssl, Homebrew installs zlib "keg-only",
you would need to explicitly reference its locations:

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

But, at the moment, both the 10.15 system zlib and the Homebrew
zlib are the same version, 1.2.11, so it doesn't seem necessary.

----------

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<https://bugs.python.org/issue40840>
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