I currently have an interesting scenario that I wonder if anyone has found 
the solution for.
We are running ansible on RHEL7 managing Windows boxes which unfortunately 
means we hit a couple of issues around pyOpenSSL versions.
We have one master playbook that imports all the other ones to run them in 
order.
The first playbook configures the localhost box ready for managing windows 
hosts and as part of this uninstall the old 0.13.x pyOpenSSL library and 
updates it to be the latest we have available that works.
We then do some chmodding to ensure permissions are correct as we've also 
seen in our circumstance that the "unable to find module xyz" errors were 
caused by ansible not having permission to access them.

At the end of this playbook execution we will still get an error that winrm 
is not installed.
However if I am then to re-run the master playbook and comment out the 
setup playbook (so that nothing changes) it will then work fine.
It seems re-running ansible causes it to detect? the new modules that we 
install and then is fine to use them.
The current solution we are running with is Jenkins runs the setup playbook 
on its own and then runs the master playbook after for everything else.

Is there a way to force ansible to effectively redetect its environment 
mid-run so we don't need to split it into two ansible calls?

Cheers

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