I believe the other issue is that Packer (or whatever libraries Packer uses 
for WinRM) does not encrypt the WinRM data so anything over http is in 
plaintext. You can disable the encryption check by running

Set-Item -Path WSMan:\localhost\Server\AllowUnencrypted -Value $true

This means that Windows will allow connections that do not encrypt the data 
but I doubt a hardened AMI would allow this change as it is quite insecure. 
What you really want to do is use a https listener which uses TLS to 
encrypt the data. This requires further steps as part of your bootstrapping 
process ot create the self-signed cert and https listener but it can be 
done. In Ansible land we use 
https://github.com/ansible/ansible/blob/devel/examples/scripts/ConfigureRemotingForAnsible.ps1
 
but you will probably need to modify it to work on your AMI.

Thanks

Jordan

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