Installing pip on macOS Sierra

Question

I've been trying to install pip on macOS sierra via brew, but every time it completes without installing the binaries in /usr/local/Cellar/python/2.7.13/bin.

I've tried:

MacBook-Pro ➜ brew reinstall python

then:

MacBook-Pro ➜  ~ which pip
pip not found

I found the path to python, which is /usr/local/Cellar/python/2.7.13/bin but no binary for pip there.

I also tried the easy_install approach:

MacBook-Pro ➜ sudo easy_install pip
Traceback (most recent call last):
  File "/usr/bin/easy_install-2.7", line 11, in <module>
    load_entry_point('setuptools==18.5', 'console_scripts', 'easy_install')()
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 352, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 2307, in load_entry_point
    return ep.load()
  File "/Library/Python/2.7/site-packages/pkg_resources.py", line 2021, in load
    entry = __import__(self.module_name, globals(),globals(), ['__name__'])
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/__init__.py", line 12, in <module>
    from setuptools.extension import Extension
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/extension.py", line 8, in <module>
    from .dist import _get_unpatched
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/setuptools/dist.py", line 21, in <module>
    packaging = pkg_resources.packaging
AttributeError: 'module' object has no attribute 'packaging'

UPDATE:

When I run brew postinstall python I am getting the following error:

MacBook-Pro ➜  ~ brew postinstall python
==> Using the sandbox
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --rec
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --rec
Last 15 lines from /Users/justin/Library/Logs/Homebrew/python/post_install.02.python:

Traceback (most recent call last):
  File "setup.py", line 92, in <module>
    cmdclass={'test': PyTest},
  File "/usr/local/Cellar/python/2.7.13/Frameworks/Python.framework/Versions/2.7/lib/python2.7/distutils/core.py", line 111, in setup
    _setup_distribution = dist = klass(attrs)
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.py", line 225, in __init__
    _Distribution.__init__(self,attrs)
  File "/usr/local/Cellar/python/2.7.13/Frameworks/Python.framework/Versions/2.7/lib/python2.7/distutils/dist.py", line 287, in __init__
    self.finalize_options()
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.py", line 258, in finalize_options
    ep.load()(self, ep.name, value)
  File "/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/pkg_resources.py", line 2020, in load
    raise ImportError("%r has no %r attribute" % (entry,attr))
ImportError: <module 'setuptools.dist' from '/Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/setuptools/dist.pyc'> has no 'check_specifier' attribute

Answer 1

Something must be wrong with your brew installation.

Latest macOS version.

 ~/ brew reinstall python
==> Reinstalling python
==> Downloading https://homebrew.bintray.com/bottles/python-2.7.13.sierra.bottle.tar.gz
Already downloaded: ~/Library/Caches/Homebrew/python-2.7.13.sierra.bottle.tar.gz
==> Pouring python-2.7.13.sierra.bottle.tar.gz
==> Using the sandbox
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --record=installed.txt --install-scripts=/usr/local/Cellar/python/2.7
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --record=installed.txt --install-scripts=/usr/local/Cellar/python/2.7
==> /usr/local/Cellar/python/2.7.13/bin/python -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --record=installed.txt --install-scripts=/usr/local/Cellar/python/2.7
==> Caveats
Pip and setuptools have been installed. To update them
  pip install --upgrade pip setuptools

You can install Python packages with
  pip install <package>

They will install into the site-package directory
  /usr/local/lib/python2.7/site-packages

See: https://github.com/Homebrew/brew/blob/master/docs/Homebrew-and-Python.md

.app bundles were installed.
Run `brew linkapps python` to symlink these to /Applications.
==> Summary
  /usr/local/Cellar/python/2.7.13: 3,526 files, 48M

And it definitely exists.

 ~/ ls -l $(which pip)
lrwxr-xr-x  1 cricket  admin  31 Dec 19 19:43 /usr/local/bin/pip -> ../Cellar/python/2.7.13/bin/pip

Answer 2

For Mac OS Sierra, cannot install pip via easy_install since there is a problem with TLS Version, Installed Open-SSL version won't support TLS 1.2

So install pip using curl as follows,

curl https://bootstrap.pypa.io/get-pip.py | sudo python

Answer 3

You just need to install pip which is not automatically installed in macOS Sierra.

Run sudo easy_install pip

Answer 4

I had this issue and I found this to be the solution. BTW pip isn't installed via brew. It comes with python and python virtualenvs.

if you type which python without brew install python you'll get the location in /usr/bin/python. That is the system python which we don't want to develop with.

So i took the following steps. 1) brew install python 2) export PATH="/usr/local/opt/python/libexec/bin:$PATH" place that in your ~/.bash_profile 3) source ~/.bash_profile in your terminal 4) type which python and that should have changed the location to /usr/local/opt/python/libexec/bin/python.

This will allow you to pip install normally and use the brew version of python.

Now before high sierra python used to be located in /usr/local/bin but for some reason if you place /usr/local/bin in your paths it automatically points back to /usr/bin, so this is the only solution I have been able to come up with.

Python3 does not have this issue, if you brew install python3 and type which python3 you'll see that it's located in /usr/local/bin/python3.

Answer 5

OK gang, lots of these answers where helpful but none of them got me to the finish line. I am running High Sierra 10.13.4. The problem as documented above is that Brew installs pip in the /usr/local/bin directory but Python is in /usr/bin (although as Carl said, Python3 correctly goes to /usr/local/bin).

My immediate use case is related to getting the Postgres BigSQL package to install.

The steps I took are as follows:

1. Clear out the brew cache $ rm -rf ~/Library/Caches/Homebrew
2. Clear out the site-packages $ sudo rm -rf /usr/local/lib/python2.7/site-packages
3. Reinstall Python $ brew reinstall python This pulls down python-3.5.6.high_sierra and put it in /usr/local/bin/python3
4. But which python still shows /usr/bin/python
5. The solution is to run brew install python@2 which pulls down [email protected]_3.high_sierra
6. Now which python shows the correct path /usr/local/bin/python which is also where all your pip stuff is installed, so now pip will work.
7. Of course if you have not installed the latest version of pip you should do that too with sudo pip install --upgrade pip

Answer 6

For what it's worth, after upgrading to high sierra I found my machine pretty much unusable for development, even crashing plenty of times.

Regarding python, i had a rights issue inside the site-packages folder, therefore the reinstall did not work out:

$ brew reinstall python

==> Reinstalling python
==> Downloading https://homebrew.bintray.com/bottles/python-2.7.14.high_sierra.bottle.tar.gz
Already downloaded: /Users/m/Library/Caches/Homebrew/python-2.7.14.high_sierra.bottle.tar.gz
==> Pouring python-2.7.14.high_sierra.bottle.tar.gz
==> /usr/local/Cellar/python/2.7.14/bin/python2 -s setup.py --no-user-cfg install --force --verbose --single-version-externally-managed --record=installed.txt --install-scripts=/usr/local/Cellar/python/2.7.14/bin --install-
Last 15 lines from /Users/m/Library/Logs/Homebrew/python/post_install.01.python2:
.
.
.
copying build/lib/setuptools/script (dev).tmpl -> /usr/local/lib/python2.7/site-packages/setuptools
copying build/lib/pkg_resources/_vendor/packaging/version.py -> /usr/local/lib/python2.7/site-packages/pkg_resources/_vendor/packaging
error: could not delete '/usr/local/lib/python2.7/site-packages/pkg_resources/_vendor/packaging/version.py': Permission denied
Warning: The post-install step did not complete successfully
...

So to fix it, I completely removed the site-packages:

$ sudo rm -rf /usr/local/lib/python2.7/site-packages

With this, reinstalling python2, and having a working pip2 again, worked like a charm:

$ brew reinstall python

$ which pip2
/usr/local/bin/pip2
$ which python2
/usr/local/bin/python2

$ which pip
pip not found
$ which python
/usr/bin/python

Hope that helps.

Answer 7

The error message has the answer for you...

Remove /Users/justin/.venvburrito/lib/python/distribute-0.6.35-py2.7.egg/ and run brew reinstall python. setuptools is the wrong version.