Cosimo Lupo <cl...@google.com> added the comment:

Hello,

I see that the official Python.org OSX 10.6+ installers are still linking with 
OSX outdated OpenSSL (0.9.8zh 14 Jan 2016; I'm using macOS High Sierra 10.13.2).

In the installer's README, they motivates this because:

> Apple's 0.9.8 version includes an important additional feature: if a 
> certificate cannot be verified using the manually administered certificates 
> in /System/Library/OpenSSL, the certificates managed by the system security 
> framework in the user and system keychains are also consulted (using Apple 
> private APIs)

However, because of this outdated OpenSSL version, I cannot use pip to install 
from the TestPyPI server https://test.pypi.org.

When I try (even with --trusted-host) I get this error:

```
$ pip install --trusted-host --index-url https://test.pypi.org/simple afdko
Collecting https://test.pypi.org/simple
Exception:
Traceback (most recent call last):
...
SSLError: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version 
(_ssl.c:661)
```

A similar issue on pypa/pip repository was closed as

> There's no actionable item here. People with old versions of openssl that 
> don't support sha1 SSL certificates need to upgrade or else they are 
> insecure. If they wish to be insecure they can continue using pip 1.2

https://github.com/pypa/pip/issues/829#issuecomment-20931050

~~~

Well, I find it particularly odd that the official binary distribution for the 
latest Python 2.7.14 has a broken (or insecure) _ssl module, even when running 
the latest macOS version.

Of course, using pyenv or homebrew fixes the problem (as they require and link 
with the latest openssl 1.0.2), but I would like to recommend installing python 
from the official binaries to my less technically-skilled colleagues of mine.

Please consider embedding the latest openssl on the 10.6+ installers like you 
already do on 10.5 32bit ones and the Windows ones, thank you.

Cosimo Lupo

----------
nosy: +Cosimo Lupo2

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