Actually after looking at the error it does still seem to be a fatal error
so I don't think the block/rescue will work in this case so I think putting
wait_for_connection after your reboot stage might be best.
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If the previous task before the copy one is to install some features and
reboot then potentially the WinRM service comes back online but it reboots
one more time that isn't caught. What I would potentially do is
- name: install problematic features
win_feature:
name: ...
register:
