Hi

It's definitely possible to install the winrm requirements with Ansible, a 
few things to note regarding your outputs

* Look at upgrading your host to a new version so that it at least has 
Python 2.7 installed by default (2.6 is old and not supported by Python 
itself but it should still work)
* Instead of installing in the system Python, use a virtualenv so you don't 
have to play around with sudo https://docs.python.org/3/library/venv.html, 
really you should be doing this, it's as simple as running *virtualenv 
ansible-venv; source ansible-venv/bin/activate*
* *pip install pywinrm* and *pip install 
http://github.com/diyan/pywinrm/archive/master.zip#egg=pywinrm* didn't work 
because you pip and setuptools version is too old, run *sudo pip install -U 
pip setuptools* to make sure you are on the latest version (note you did 
this already but I would also try and upgrade pip at the same time)
* Finally your last error is because it needs root privileges to install 
the pycparser (and probably others) in the system Python packages, you 
would either run it with *pip install --user ...* or *sudo pip install ...*, 
or better yet use a venv and you won't have to worry about this issue
* Not related but it makes it a lot easier to see what commands you ran by 
using the code block formatting with Google Groups posts, the button with 
the 2 braces *{ } *will do the highlighting for you and it is best to put 
each command in it's own code block

Looking at some of the warnings, it seems like SSL isn't configured 
correctly with the Python 2.6 install so I would really look at my first 
point and try a newer host, as you are using Vagrant I don't see why this 
should be avoided and you can potentially save yourself some more trouble 
down the road.

Thanks

Jordan

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