Chef - Waiting for remote response before bootstrap.error: failed to authenticate to [REMOTE_HOST] as [ADMINISTRATOR]

Hey Community,

I am just left scratching my head with this... The same username and password I use to RDP into the AWS remote node I use to bootstrap the node and yet it fails. What could I be missing here?

  • I test to make sure that port 5985 is listening on the remote host and it is.
  • I test other servers that I have CHEF'ed to make sure that I can still run remote commands using knife and I can
  • I noticed that I only have this problem WITH Windows server 2016. I DONT have this problem with Windows server 2012 (so far).
  • I noticed this as of yesterday (Sept, 16th, 2019)

This seems to be isolated to windows server 2016, but why? What are you folks doing to bootstrap windows server 2016?

knife bootstrap windows winrm '[REMOTE_HOST_IP]' -y -N '[REMOTE_NODE_NAME]' -x 'localhost\administrator' -P "[REMOTE_HOST_PW]" --runlist 'role[ROLENAME]' --bootstrap-install-command 'msiexec /i http://[SERVER_IP]/chef-client.msi'

Help! :slight_smile:

Thank you in advise,

You may need to setup winrm and make sure firewall rules are set correctly.
There are a few troubleshooting steps here:

Hope that helps!