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Pax
I have a CentOS 6.8 VM through Vagrant and when I attempt to use pip it gives me an error:

```sh
[vagrant@localhost Python-3.8.6]$ python3.8 -m pip install --user pipx
WARNING: pip is configured with locations that require TLS/SSL, however the ssl module in Python is not available.
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not available.")': /simple/pipx/
WARNING: Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not available.")': /simple/pipx/
WARNING: Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not available.")': /simple/pipx/
WARNING: Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not available.")': /simple/pipx/
WARNING: Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError("Can't connect to HTTPS URL because the SSL module is not available.")': /simple/pipx/
Could not fetch URL https://pypi.org/simple/pipx/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pipx/ (Caused by SSLError("Can't connect to HTTPS URL because the SSL module is not available.")) - skipping
ERROR: Could not find a version that satisfies the requirement pipx (from versions: none)
ERROR: No matching distribution found for pipx
WARNING: pip is configured with locations that require TLS/SSL, however the ssl module in Python is not available.
Could not fetch URL https://pypi.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by SSLError("Can't connect to HTTPS URL because the SSL module is not available.")) - skipping
```

The Vagrant VM is created using a Vagrantfile, and python is installed through a series of commands. For the curious, both Vagrantfile and list of commands are found in this [gist](https://gist.github.com/paxcodes/32a22537165a4ddd2bc45318df6fa4e8).

Some observations:

* As seen in the gist, I installed the following dependencies before installing python; they all installed without errors.

```
yum groupinstall -y "development tools"

yum install -y zlib-devel bzip2-devel openssl-devel ncurses-devel sqlite-devel readline-devel tk-devel gdbm-devel db4-devel libpcap-devel xz-devel expat-devel
```
* Python 3.8.6 is successfully installed

```sh
[vagrant@localhost ~]$ python3.8 -V
Python 3.8.6
```

* OpenSSL is installed

```sh
[vagrant@localhost ~]$ openssl version -a
OpenSSL 1.0.1e-fips 11 Feb 2013
built on: Wed Aug 14 16:32:19 UTC 2019
platform: linux-x86_64
```

What am I missing?
Top Answer
Pax
The OpenSSL 1.1.1 is required for Python 3.8.

As seen in this [message in Python-Dev](https://mail.python.org/pipermail/python-dev/2019-February/156470.html) mailing list.

> Python 3.7 and master (3.8) are affected [by the OpenSSL 1.1.1 update]. As of now, both branches use OpenSSL 1.1.0 and must be updated to 1.1.1 soonish.

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