In a nutshell, 'vagrant up' 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.*

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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