I can't say why it isn't working as most of the time I avoid Cygwin due to 
issues like these. One thing you should look into is changing your 
win_command tasks from

- win_command: cmd.exe /c "start something.exe"

to just

- win_command: something.exe

For example your 2nd task would look like

- name: Run chmod script 2
  win_command: C:\cygwin\bin\bash.exe /cygdrive/c/TEMP/chmod2.sh

What you are effectively doing in your examples, is starting a new cmd 
process (cmd.exe) and then getting that to start another executable 
(C:\cygwin\bin\bash.exe), there is no point in this as win_command is 
designed to run executables and all you are doing is adding another layer 
that could be causing trouble.

As for the issue itself, I would think it could be that you are running it 
as the SYSTEM account and from a cygwin user permissions perspective it is 
unable to access the home directory for YRunner. While SYSTEM pretty much 
has full rights in Windows, I'm unsure how that translates to Cygwin and to 
me seems to be the reason why it may be failing.

Thanks

Jordan

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