python and python@2 can build on Mac 10.14, but zlib is not found, which breaks pip

[jnozsc]

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• ran brew update and can still reproduce the problem?
• ran brew doctor, fixed all issues and can still reproduce the problem?
• ran brew gist-logs <formula> (where <formula> is the name of the formula that failed) and included the output link?
• if brew gist-logs didn't work: ran brew config and brew doctor and included their output with your issue?

To help us debug your issue please explain:

• What you were trying to do (and why)
  I do brew upgrade today, and python@2 and python, which previously install on Mac 10.13, get updated and build with 10.14 environment

• What happened (include command output)
  After the install finish without any error,
  when I run python or python3, it still works
  but when I run pip or pip3, I get the following error message

Traceback (most recent call last):
  File "/usr/local/bin/pip3", line 11, in <module>
    load_entry_point('pip==10.0.1', 'console_scripts', 'pip3')()
  File "/usr/local/lib/python3.6/site-packages/pkg_resources/__init__.py", line 476, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/usr/local/lib/python3.6/site-packages/pkg_resources/__init__.py", line 2700, in load_entry_point
    return ep.load()
  File "/usr/local/lib/python3.6/site-packages/pkg_resources/__init__.py", line 2318, in load
    return self.resolve()
  File "/usr/local/lib/python3.6/site-packages/pkg_resources/__init__.py", line 2324, in resolve
    module = __import__(self.module_name, fromlist=['__name__'], level=0)
  File "/usr/local/lib/python3.6/site-packages/pip/_internal/__init__.py", line 20, in <module>
    from pip._vendor.urllib3.exceptions import DependencyWarning
  File "/usr/local/lib/python3.6/site-packages/pip/_vendor/urllib3/__init__.py", line 8, in <module>
    from .connectionpool import (
  File "/usr/local/lib/python3.6/site-packages/pip/_vendor/urllib3/connectionpool.py", line 36, in <module>
    from .response import HTTPResponse
  File "/usr/local/lib/python3.6/site-packages/pip/_vendor/urllib3/response.py", line 3, in <module>
    import zlib
ModuleNotFoundError: No module named 'zlib'

• What you expected to happen
  pip and pip3 should work

• Step-by-step reproduction instructions (by running brew install commands)
  here is my brew gist-logs python 's output

https://gist.github.com/jnozsc/afa4e8d3d7e8b827ddc009e482560bb2

I assume this maybe related with Homebrew/brew#4335 , but I tried to rebuild either python@2 or pyhon with this branch, still not work

[ilovezfs]

You have the CLT headers installed so I'm not sure how Homebrew/brew#4335 would be relevant.

[mistydemeo]

Hm, I can't reproduce this on the master branch of both Homebrew and homebrew-core.

Was your first test on the latest commit of master for Homebrew and homebrew-core? Is there a file named /usr/include/zlib.h?

[jnozsc]

I tried reinstall everything this morning after upgrade to 10.14 developer preview 2, it seems I can not reproduce this issue either. I think I may mess up my environment before.

Close due to unable to reproduce

[sfdye]

I have the same issue with zlib not found.

This worked for me:

1. brew update
2. (Re)Install CLT. installer -pkg /Library/Developer/CommandLineTools/Packages/macOS_SDK_headers_for_macOS_10.14.pkg -target /
3. brew reinstall python@2

[zedtux]

I'm able to reproduce this issue, even with the Beta 2.

If I can help, please let me know what I can do.

[zedtux]

I followed instructions from @sfdye and python@2 was successfully installed, which also solved my issue from #29245. 🎉

[narner]

I'm currently having the same issue - have tried the instructions from @sfdye that @zedtux said they got working. Currently getting the following error after brew reinstall Python@2:

==> Reinstalling python@2 
==> Downloading https://www.python.org/ftp/python/2.7.15/Python-2.7.15.tar.xz
Already downloaded: /Users/nicholasarner/Library/Caches/Homebrew/python@2-2.7.15.tar.xz
==> ./configure --prefix=/usr/local/Cellar/python@2/2.7.15_1 --enable-ipv6 --datarootdir=/usr/l
==> make
==> make install PYTHONAPPSDIR=/usr/local/Cellar/python@2/2.7.15_1
==> make frameworkinstallextras PYTHONAPPSDIR=/usr/local/Cellar/python@2/2.7.15_1/share/python@
==> Downloading https://files.pythonhosted.org/packages/1a/04/d6f1159feaccdfc508517dba1929eb93a
Already downloaded: /Users/nicholasarner/Library/Caches/Homebrew/python@2--setuptools-39.2.0.zip
==> Downloading https://files.pythonhosted.org/packages/ae/e8/2340d46ecadb1692a1e455f13f75e596d
Already downloaded: /Users/nicholasarner/Library/Caches/Homebrew/python@2--pip-10.0.1.tar.gz
==> Downloading https://files.pythonhosted.org/packages/2a/fb/aefe5d5dbc3f4fe1e815bcdb05cbaab19
Already downloaded: /Users/nicholasarner/Library/Caches/Homebrew/python@2--wheel-0.31.1.tar.gz
==> make html
Last 15 lines from /Users/nicholasarner/Library/Logs/Homebrew/python@2/05.make:
    return build_main(argv)
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/cmd/build.py", line 22, in build_main
    from sphinx import cmdline
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/cmdline.py", line 23, in <module>
    from sphinx.application import Sphinx
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/application.py", line 29, in <module>
    from sphinx.config import Config
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/config.py", line 21, in <module>
    from sphinx.util import logging
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/util/__init__.py", line 33, in <module>
    from sphinx.util import logging
  File "/usr/local/Cellar/sphinx-doc/1.7.5_1/libexec/lib/python2.7/site-packages/sphinx/util/logging.py", line 106, in <module>
    class SphinxLoggerAdapter(logging.LoggerAdapter):
AttributeError: 'module' object has no attribute 'LoggerAdapter'
make: *** [build] Error 1

Do not report this issue to Homebrew/brew or Homebrew/core!

These open issues may also help:
python 3.7.0 https://github.com/Homebrew/homebrew-core/pull/29490
python upgrade failing https://github.com/Homebrew/homebrew-core/issues/29214
app-engine-python 1.9.70 https://github.com/Homebrew/homebrew-core/pull/28858
molecule: Use correct `docker` python package dependency https://github.com/Homebrew/homebrew-core/pull/28635
[root] formula does not link against python@2 correctly. https://github.com/Homebrew/homebrew-core/issues/29377
clingo add support for lua, use python 3 https://github.com/Homebrew/homebrew-core/pull/28057
OSError: [Errno 1] Operation not permitted for python@2 –with-tcl-tk https://github.com/Homebrew/homebrew-core/issues/28168

Error: You are using macOS 10.14.
We do not provide support for this pre-release version.
You may encounter build failures or other breakages.
Please create pull-requests instead of filing issues.

Error: You are using macOS 10.14.
We do not provide support for this pre-release version.
You may encounter build failures or other breakages.
Please create pull-requests instead of filing issues.

[zedtux]

@narner you have a complete different issue than what has been reported in this issue. You should open a new one in my opinion.

Sorry for not being helpful 😞

[muammar]

I am getting the same problem. I upgraded to Mojave beta public preview. Reinstalling python2 as suggested by @sfdye didn't work for me. As pointed out by @mistydemeo, I don't have /usr/include/zlib.h file present on my installation:

muammar@zarathustra ~
  % file /usr/include/zlib.h                                                                                                                           !10161
/usr/include/zlib.h: cannot open `/usr/include/zlib.h' (No such file or directory)

I proceeded to do a brew install zlib and a brew reinstall python and that did not work either.

[ruchernchong]

@muammar you might want to try it, since there was an issue with a fix referenced after your comment.