I finally figured out what's going on. I'm using the same machine as 
Guilhem Brouat was, the vagrant-win7-ie8 box. This box is not configured 
properly to be used by Vagrant, because the Modern.ie team released it 
before Windows was supported  (I think?). Their goal was just to have a VM 
that could be spun up with "vagrant up" and then interacted with *manually*. 
It isn't set up to be accessed via SSH or WinRM.

If you follow the steps here on the original 
box: https://gist.github.com/uchagani/48d25871e7f306f1f8af

Then repackage the box using

 vagrant package --output vagrant-win7-ie8-updated.box


Then add the new box using 

vagrant box add vagrant-win7-ie8-updated vagrant-win7-ie8-updated.box


It will spin up properly as long as you have a good Vagrantfile.

For reference, here is my Vagrantfile:

 

# -*- mode: ruby -*-

# vi: set ft=ruby :


>
> VAGRANTFILE_API_VERSION = "2"


> Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|


>   config.vm.define "win7" do |win7|

    # 
> http://blog.syntaxc4.net/post/2014/09/03/windows-boxes-for-vagrant-courtesy-of-modern-ie.aspx

    win7.vm.box = "vagrant-win7-ie8-updated"

    win7.vm.guest = :windows


>     win7.vm.network :forwarded_port, guest: 3389, host: 3391

    win7.vm.network :forwarded_port, guest: 5985, host: 5987, id: "winrm", 
> auto_correct: true


>     win7.windows.set_work_network = true

    # Makes the host machine available as "192.168.50.1" on the guest

    win7.vm.network "private_network", ip: "192.168.50.2"


>     # 
> http://stackoverflow.com/questions/23574387/why-is-vagrant-trying-to-ssh-to-windows-guest

    # 
> https://www.vagrantup.com/blog/feature-preview-vagrant-1-6-windows.html

    win7.vm.communicator = "winrm"


>     win7.winrm.username = "IEUser"

    win7.winrm.password = "Passw0rd!"


>     # We don't want the default headless mode

    win7.vm.provider "virtualbox" do |vb|

      vb.gui = true

    end

  end


What's still unfortunate is that there isn't a way to automate that process 
(except with something like Sikuli).

On Sunday, February 15, 2015 at 3:11:19 PM UTC-5, Umair Chagani wrote:
>
> If you search the Issues list there is a bug with Windows guests. I would 
> downgrade to Vagrant v1.6.5
> On Feb 15, 2015 2:27 PM, "Tom Jacques" <[email protected] <javascript:>> 
> wrote:
>
>> +1 I've been trying for hours to get one of these set up, so far no dice. 
>> I'm wondering if anyone's been able to do it, or if it requires modifying 
>> the VM image.
>>
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