Upgrading to Ansible 2.2.1 on Debian (validated on version 8.7) requires some pre-requisites to be in place, below are the steps required to upgrade.
Ensure that sudo is installed (skip this step if you already know that it is):
apt-get install sudo
Upgrade all packages:
sudo apt-get update
sudo apt-get upgrade
Install build pre-requisites:
sudo apt-get install build-essential libssl-dev libffi-dev python-dev
Upgrade to the latest version of the Cryptography module:
sudo pip install cryptography --upgrade
If you encounter errors with the above command, run the following to reinstall PIP from the official PIP website as referred to at https://github.com/pypa/get-pip.
sudo apt-get purge -y python-pip
sudo wget https://bootstrap.pypa.io/get-pip.py
sudo python ./get-pip.py
sudo apt-get install python-pip
Finally, upgrade Ansible to the latest version:
sudo pip install ansible --upgrade
