This article shows how to solve the pip and ssl version problem when install Pillow:

1. The environment

  • Python 2.7.10
  • OS: Mac OS 10.12.4

2. The problem

➜  bswen: pip install pillow
Collecting pillow
  Could not fetch URL https://pypi.python.org/simple/pillow/: There was a problem confirming the ssl certificate: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590) - skipping
  Could not find a version that satisfies the requirement pillow (from versions: )
No matching distribution found for pillow

3. The reason

After google, I found the reason is:

The ssl support is deprecated in the pip(version 9.*),you should upgrade to pip 10

3. Solve the problem

So I installed pyenv like this:

➜  bswen: brew install pyenv

And Then add this script to ~/.zshrc

eval "$(pyenv init -)"

And then quit the terminal and install the new python version:3.6.5

➜  bswen: pyenv install 3.6.5

And then set the local version to 3.6.5

➜  bswen: pyenv local 3.6.5

Verify the version:

➜  bswen: python --version
Python 3.6.5

Upgrade to pip 10:

➜  bswen: pip install --upgrade pip

At last, we install the Pillow like this:

➜  bswen: pip install Pillow

Verify the pillow installation:

➜  bswen: python
Python 3.6.5 (default, Apr 22 2018, 14:43:19)
[GCC 4.2.1 Compatible Apple LLVM 8.0 (clang-800)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
>>> import PIL
>>>

The pillow is installed successfully.

You can find detail documents about the python pip here: