pipenv-only TLS issue on macOS

pipenv is failing due to TLS issues on a new High Sierra 10.13.4 system with python 2.7.14 from python.org’s pkg installed. I have updated pip to support the latest TLS.

FYI someone mentioned this issue before but closed their issue because it “resolved itself” without explanation.

$ pip --version
pip 10.0.1 from /Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/site-packages/pip (python 2.7)

$ python -c "import ssl; print(ssl.OPENSSL_VERSION)"
OpenSSL 0.9.8zh 14 Jan 2016

$ python -m pipenv.help output

Pipenv version: '11.10.1'

Pipenv location: '/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/site-packages/pipenv'

Python location: '/Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python'

Other Python installations in PATH:

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2.7

• 2.7: /usr/local/bin/python2.7

• 2.7: /usr/bin/python2.7

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python

• 2.7.14: /usr/local/bin/python

• 2.7.10: /usr/bin/python

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2

• 2.7.14: /Library/Frameworks/Python.framework/Versions/2.7/bin/python2

• 2.7.14: /usr/local/bin/python2

PEP 508 Information:

{'implementation_name': 'cpython',
 'implementation_version': '0',
 'os_name': 'posix',
 'platform_machine': 'x86_64',
 'platform_python_implementation': 'CPython',
 'platform_release': '17.5.0',
 'platform_system': 'Darwin',
 'platform_version': 'Darwin Kernel Version 17.5.0: Fri Apr 13 19:32:32 PDT 2018; root:xnu-4570.51.2~1/RELEASE_X86_64',
 'python_full_version': '2.7.14',
 'python_version': '2.7',
 'sys_platform': 'darwin'}

System environment variables:

• PYTHONIOENCODING
• TERM_PROGRAM_VERSION
• PLAYERGLOBAL_HOME
• SCALA_HOME
• LOGNAME
• USER
• HOME
• PS2
• PATH
• PS1
• PS4
• TERM_PROGRAM
• LANG
• TERM
• SHELL
• COLORFGBG
• SHLVL
• XPC_FLAGS
• HISTSIZE
• ITERM_SESSION_ID
• _
• MANPATH
• JBOSS_HOME
• M2_HOME
• HISTFILESIZE
• TERM_SESSION_ID
• XPC_SERVICE_NAME
• SSH_AUTH_SOCK
• DYLD_LIBRARY_PATH
• Apple_PubSub_Socket_Render
• PYTHONDONTWRITEBYTECODE
• ITERM_PROFILE
• PIP_PYTHON_PATH
• TMPDIR
• ANT_HOME
• LC_COLLATE
• __CF_USER_TEXT_ENCODING
• PWD
• COLORTERM

Pipenv–specific environment variables:

Debug–specific environment variables:

• PATH: /Library/Frameworks/Python.framework/Versions/2.7/bin:/Library/Frameworks/Python.framework/Versions/3.6/bin:/Library/Frameworks/Python.framework/Versions/2.7/bin:/Library/Frameworks/Python.framework/Versions/3.6/bin:/Library/Frameworks/Python.framework/Versions/2.7/bin:/Library/Frameworks/Python.framework/Versions/3.6/bin:/Library/Frameworks/Python.framework/Versions/2.7/bin:/Library/Frameworks/Python.framework/Versions/3.6/bin:/Users/rick/notes/scripts:/Users/rick/bin::/opt/make/4.2.1/bin:/Users/rick/Library/Python/3.6/bin:/Users/rick/Library/Python/2.7/bin:/Library/Frameworks/Python.framework/Versions/3.6/bin:/Library/Frameworks/Python.framework/Versions/2.7/bin:/opt/openssh/7.6p1/bin:/opt/rar/5.2.1/bin:/opt/redis/3.2.8/bin:/opt/node/6.10.0/bin:/Users/rick/.npm-packages/bin:/opt/mongodb/2.4.10/bin:/opt/ffmpeg/3.4-evermeet:/opt/ImageMagick/6.8.8/bin:/opt/apache/flex-sdk/4.14.0/bin:/opt/jq/1.5/bin:/opt/elasticsearch/1.4.3/bin:/opt/kibana/4.1.2/bin:/opt/postgresql/9.6.2/bin:/opt/ruby/2.5.1/bin:/opt/aria2/1.31.0/bin:/opt/phantomjs/2.1.1/bin:/opt/git-lfs/1.5.5/bin:/opt/google-cloud-sdk/143.0.1/bin:/opt/pandoc/1.19.2.1/bin:/opt/autotools/bin:/opt/openssl/1.0.2m/bin:/opt/icu/58.2/bin:/opt/fop/2.2/fop:/opt/wxWidgets/3.0.3/bin:/opt/erlang/20.2/bin:/opt/yaws/1.99/bin:/opt/apache/ant/1.9.4/bin:/opt/maven/3.3.3/bin:/opt/spark/1.2.0/bin:/opt/sbt/0.13.7/bin:/opt/mysql/5.7.17/bin:/opt/xz/5.2.3/bin:/opt/watchman/4.7.0/bin:/opt/pv/1.6.0/bin:/opt/sassc/3.4.2/bin:/opt/cpdf/2.2/bin:/Applications/CMake.app/Contents/bin:/opt/cmark/0.28.3/bin:/opt/cmark-gfm/0.28.0.gfm.11/bin:/opt/p7zip/16.02/bin:/opt/heroku/20170629/bin:/opt/monero/0.11.1.0:/usr/local/bin:/usr/bin:/bin:/usr/sbin:/sbin:/Library/TeX/texbin
• SHELL: /bin/bash
• LANG: en_US.UTF-8
• PWD: /Users/rick

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Expected result

$ pipenv install -r requirements.txt
Creating a virtualenv for this project…
Using /Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python (2.7.14) to create virtualenv…
⠋Already using interpreter /Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python
New python executable in /Users/rick/.local/share/virtualenvs/voice-quickstart-server-python-zVwW_i1A/bin/python
Installing setuptools, pip, wheel...done.

Virtualenv location: /Users/rick/.local/share/virtualenvs/voice-quickstart-server-python-zVwW_i1A
Creating a Pipfile for this project…
Requirements file provided! Importing into Pipfile…
Pipfile.lock not found, creating…
Locking [dev-packages] dependencies…
Locking [packages] dependencies…
... sunshine and rainbows ...
Done.

Actual result

$ pipenv install -r requirements.txt
Creating a virtualenv for this project…
Using /Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python (2.7.14) to create virtualenv…
⠋Already using interpreter /Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python
New python executable in /Users/rick/.local/share/virtualenvs/voice-quickstart-server-python-zVwW_i1A/bin/python
Installing setuptools, pip, wheel...done.

Virtualenv location: /Users/rick/.local/share/virtualenvs/voice-quickstart-server-python-zVwW_i1A
Creating a Pipfile for this project…
Requirements file provided! Importing into Pipfile…
Pipfile.lock not found, creating…
Locking [dev-packages] dependencies…
Locking [packages] dependencies…
/Library/Python/2.7/lib/python/site-packages/pipenv/vendor/requests/sessions.py", line 508, in request
    resp = self.send(prep, **send_kwargs)
  File "/Users/rick/Library/Python/2.7/lib/python/site-packages/pipenv/vendor/requests/sessions.py", line 618, in send
    r = adapter.send(request, **kwargs)
  File "/Users/rick/Library/Python/2.7/lib/python/site-packages/pipenv/vendor/requests/adapters.py", line 506, in send
    raise SSLError(e, request=request)
requests.exceptions.SSLError: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /pypi/itsdangerous/json (Caused by SSLError(SSLError(1, u'[SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:661)'),))

/Users/rick/Library/Python/2.7/lib/python/site-packages/pipenv/utils.py:1288: ResourceWarning: Implicitly cleaning up <TemporaryDirectory '/var/folders/7x/pfyb8v_j13bdvsj9rrgftq8w0000gn/T/pipenv-L14PsE-requirements'>
  warnings.warn(warn_message, ResourceWarning)

Steps to replicate

• new macOS High Sierra 10.13.4
• install Python 2.7.14 from python.org here: https://www.python.org/ftp/python/2.7.14/python-2.7.14-macosx10.6.pkg
• update pip with curl https://bootstrap.pypa.io/get-pip.py -O; sudo python get-pip.py
• go into project with this requirements.txt file:

Flask==0.10.1
Jinja2==2.7.3
MarkupSafe==0.23
Werkzeug==0.9.6
httplib2==0.9
itsdangerous==0.24
six==1.*
twilio==6.10.0
wsgiref==0.1.2
nose
requests
pyjwt

• run pipenv install -r requirements.txt

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[GregOwen]

For anyone running into this issue, I was able to fix the problem and successfully use pipenv install after doing the following:

1. Uninstall pipenv
2. brew install python2 python3
3. ls /usr/bin/python* (or wherever your system Python is installed)
4. For each binary in the result of the above ls command, find the corresponding binary that Brew installed (/usr/local/bin/python* for me) and perform ln -sf /path/to/brew/binary /path/to/system/binary (this will overwrite the system binary)

I hope this helps!

[siowyisheng]

Uninstalling and reinstalling with brew install pipenv worked for me. Thanks!