Vagrant windows 8.1 box timeouts - even though the machine boots correctly

Question

I have a simple vagrant master box, that has Windows, drivers for it, and VB guest additions installed.

I've added that machine as a box, and tried creating a simple vagrant vm with only the basic settings:

# -*- mode: ruby -*-
# vi: set ft=ruby :

# Vagrantfile API/syntax version. Don't touch unless you know what you're doing!
VAGRANTFILE_API_VERSION = "2"

Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|
  config.vm.box = "win"
  config.vm.communicator = "winrm"
end

When I do Vagrant up I get timeout:

C:\Vagrant\win-dev> vagrant up Bringing machine 'default' up with 'virtualbox' provider...
==> default: Importing base box 'win'...
==> default: Matching MAC address for NAT networking...
==> default: Setting the name of the VM: win-dev_default_1415127726713_75064
==> default: Fixed port collision for 5985 => 55985. Now on port 2200.
==> default: Clearing any previously set network interfaces...
==> default: Preparing network interfaces based on configuration...
    default: Adapter 1: nat
==> default: Forwarding ports...
    default: 5985 => 2200 (adapter 1)
    default: 22 => 2222 (adapter 1)
==> default: Booting VM...
==> default: Waiting for machine to boot. This may take a few minutes...

It hangs there for a few minutes and then I get error:

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.

I'm watching the Preview window and I can clearly see that the machine is correctly booted up and waits for user input on desktop, but Vagrant is not aware of that.

I did search a lot and I found people having similar issues before but they were all related to ssh access.

EDIT: I've also tried with Windows8.1 box from vagrantbox.es and a random one from vagrantcloud, getting the same problem, so I'm pretty sure it's a configuration issue. I've also tried following a simplest guide on the Vagrantup site and getting the same error. Also tried on a different host, no luck.

Answer 1

There's a bug in Vagrant that's been fixed, but is yet unreleased that allows vagrant to fail fast and properly output the error.

Until then double check that you can login to the box using the username and password which vagrant is using, by default the username and password are both "vagrant". Changing the windows password is a common cause of this problem. Also double check the winrm configuration on the guest is setup to allow basic auth over http.