I'm a bit confused, do you need to use Cygwin to run this script, 
everything would be so much simpler if you ignored Cygwin and used 
something like PowerShell or pure Python? For your current playbook there 
are a few issues I see;

   - Windows modules, like win_template, do not support the mode/owner 
   options when it comes to files. Windows uses a more complex setup using 
   ACLs which don't map neatly with the traditional unix permissions
   - You are connecting over WinRM (not SSH in cygwin), unix-isms like ~/ 
   may work but not strictly Windows and may not work in all cases. The path 
   to ~/ is not necessarily the same path when you are in cygwin, e.g. it's 
   probably going to be a path in the user directory
   - The raw module invocation is expecting to be in a cygwin environment 
   as you are calling a bash script, you are actually in a PowerShell 
   environment and need to explicitly call C:\cygwin\bin\bash.exe (or wherever 
   it is located) to execute the bash script in cygwin

What I would do is get rid of the bash script and just execute the Python 
scripts you have directly in Windows.

Thanks

Jordan

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