1) Some questions and a guess:What version of knife-windows are you using?
Are you really logging in as plain administrator, or are you using a domain account?
Are you running this on a Windows workstation?
If your answers are "0.8.4", "yes plain local Administrator", and "yes, windows workstation", then try this instead:
knife bootstrap windows winrm 'server.nightly.bla' -r 'app::base' -x .\administrator -P 'xyz'
That is, specify .\Administrator instead of Administrator. In 0.8.4 this triggers the use of the negotiate protocol for authentication.
2) You can also use these commands to test your remote winrm configuration:This should give you a few lines of text that doesn't look like an error (change the IP):test-wsman 192.158.5.105
Run this in powershell, enter Administrator and the password on the remote machine$Credential = Get-CredentialYou'll need to trust the remote machine probably for the following tests. The output for test-wsman should be similar to the last time you ran it.winrm set winrm/config/client '@{TrustedHosts="192.168.5.105"}'test-wsman 192.168.5.105 -Authentication Basic -Credential $Credentialtest-wsman 192.168.5.105 -Authentication Negotiate -Credential $Credential3) Finally if you're still having problems, run and share the output of "winrm get winrm/config/service"
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