Hi,
 
I had a similar issue.
My box was working fine with Vagrant1.5.1 after installing 1.6.1 i faced 
this issue 
 
In  vagrant 1.6.1 the vagrant-windows plugin should be present along with 
vagrant. But, its not working.
So, I installed vagrant-windows plugin 1.6.0 it works fine.
 
 
On Saturday, May 10, 2014 12:20:26 AM UTC+5:30, akshtray wrote:

> In a nutshell, 'vagrant up' is running into an issue where I keep getting:
>
> *    default: SSH address: 127.0.0.1:2222 <http://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.*
>
> However, the box does come up just fine and is usable. To give some 
> details and background (lots of information down there):
>
> I have Vagrant 1.6.1 and VirtualBox 4.3.10r93012 running on my work laptop 
> which is running Windows 7 Professional (64 bit). I have a Base Box for 
> Windows 2008 Server (64 bit) created and in place. I made sure to do the 
> following on the Windows VM (in Virtualbox) before packaging/creating the 
> Base Box using 'vagrant package':
>
> Created a OS user called "vagrant" with password "vagrant". Made it 
> 'Administrator'
> Turned off UAC (Msconfig)
> Disabled complex passwords.
> Disabled Shutdown Tracker.
> Disabled "Server Manager" Starting at login.
> Enabled and configured WinRM.
>
> My Vagrant file is fairly simple:
> *********
> Vagrant.configure("2") do |config|
>
>   # Max time to wait for the guest to shutdown
>   config.windows.halt_timeout = 60
>   config.windows.set_work_network = true
>   
>   # 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 = "./BaseBox.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
> end
> *********
>
> Things I have tried unsuccesfully:
>
> 1. 'vagrant reload' 
> 2. 'vagrant destory' -> modify vagrantfile -> 'vagrant up'. Some of the 
> things I tried:
>
> - config.windows.set_work_network = true
> - config.vm.network "private_network", type: "dhcp"
> - config.ssh.password = "vagrant" -- tried forcing it to use password 
> instead of keys for authentication.
>
> 3. Tried using 'NAT' and 'Bridged' both for the Network adapters on the VM 
> before packaging them.
>
> To test, I tried to create a brand new VM using:
>
> vagrant init hashicorp/precise64
> vagrant up
>
> This worked great and I ran into no issues. I am really out of ideas at 
> this point of time regarding what else I can try.
>
> Help will be greatly appreciated.
>
> Thanks.
>

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