Why is Vagrant trying to SSH to Windows guest

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My host is running Windows 7 Pro (64 bit). The Guest OS in this case is Windows Server 2008 R2. The 'vagrant up' command is running into an issue where I keep getting:

****default: SSH address: 127.0.0.1:2222
default: SSH username: vagrant
default: SSH auth method: password
default: Warning: Connection timeout. Retrying...
default: Warning: Remote connection disconnect. Retrying...
default: Warning: Remote connection disconnect. Retrying...
default: Warning: Remote connection disconnect. Retrying...
default: Warning: Remote connection disconnect. Retrying...****

till it eventually times out and says:

Timed out while waiting for the machine to boot. This means that
Vagrant was unable to communicate with the guest machine within
the configured ("config.vm.boot_timeout" value) time period.
If you look above, you should be able to see the error(s) that
Vagrant had when attempting to connect to the machine. These errors
are usually good hints as to what may be wrong.
If you're using a custom box, make sure that networking is properly
working and you're able to connect to the machine. It is a common
problem that networking isn't setup properly in these boxes.
Verify that authentication configurations are also setup properly,
as well.
If the box appears to be booting properly, you may want to increase
the timeout ("config.vm.boot_timeout") value.

The VM actually comes up fine, is accessible and usable.

  • Why is it trying to even SSH to the Windows machine?

My Vagrantfile contents are:

Vagrant.configure("2") do |config|

  # Max time to wait for the guest to shutdown
  config.windows.halt_timeout = 60

  # Admin user name and password
  config.winrm.username = "Administrator"
  config.winrm.password = "Password"

  # Configure base box parameters
  config.vm.box = "BaseBox"
  config.vm.box_url = "./Base.box"
  config.vm.guest = :windows
  config.vm.provider "virtualbox" do |v|
    v.gui = true
  end

  # Port forward WinRM and RDP (changed values to NOT conflict with host)
  config.vm.network :forwarded_port, guest: 3389, host: 3391
  config.vm.network :forwarded_port, guest: 5985, host: 5987, id: "winrm", auto_correct: true

end

Best Answer

You need to use 

   config.vm.communicator = "winrm"

In your vagrant file. Take a look at this feature preview

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