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 -- You received this message because you are subscribed to the Google Groups "Ansible Project" group. To unsubscribe from this group and stop receiving emails from it, send an email to ansible-project+unsubscr...@googlegroups.com. To post to this group, send email to ansible-project@googlegroups.com. To view this discussion on the web visit https://groups.google.com/d/msgid/ansible-project/cfd57140-b674-4f92-b932-4dec63d3a9c0%40googlegroups.com. For more options, visit https://groups.google.com/d/optout.