It turned out to be a permissions issues. Somehow the permissions of the 
MachineKeys directory had changed on my Host Box. The administrators group 
didn't have permissions to the folder. Windows was trying to create a new 
cert but was failing due to the lack of permissions.

On Thursday, June 25, 2015 at 1:16:49 PM UTC-5, dragon788 wrote:
>
> This sounds more like there is a firewall setting on the host that was 
> changed and is blocking 3389 or something turned off the remote desktop 
> services. You can check in Virtualbox under Network>NAT to see if there are 
> any port mappings on 3389 and delete them, but it feels more likely that 
> the network interface type of Local Area Connection got changed to public 
> which enabled the firewall and is blocking RDP.
>
> On Wednesday, June 24, 2015 at 8:26:50 PM UTC-5, Gerane wrote:
>>
>> I am using vagrant + virtualbox. I have this set up in my vagrant fie.
>>
>> It is set to auto-correct in my vagrant file and usually maps to 2222. I 
>> can have all vagrant VMs destroyed yet my Host 3389 still cannot be 
>> accessed. I would think that even if there was some sort of conflict having 
>> all vagrant VMs destroyed should clear up any port forwardings? 
>>
>> The only thing I can think of was a few test boxes I fired up for testing 
>> when I first installed vagrant. I just downloaded them from vagrant and 
>> used their default configs. These did not have port forwarding properly set 
>> up. I then edited their vagrant files to properly use auto correct. 
>> However, my 3389 is still broken.
>>
>> Is there a way to check for any hung configurations or force defaults?
>>
>> On Wednesday, June 24, 2015 at 2:30:41 PM UTC-5, dragon788 wrote:
>>>
>>> Using Vagrant + VMware or Vagrant + Virtualbox? Primarily I'd suggest 
>>> setting up your port forwardings in the vagrant file to avoid conflicting 
>>> with the host's ports, and technically Vagrant should be doing this already 
>>> if you are on a Windows host it will avoid 3389 and other "in use" ports, 
>>> as on Linux it avoids 22 and some others.
>>>
>>> On Tuesday, June 23, 2015 at 1:52:18 PM UTC-5, Gerane wrote:
>>>>
>>>> After running a few Vagrant VMs I am no longer able to RDP into the 
>>>> Host. This remains true even if all Vagrants VMs have been destroyed. This 
>>>> was not an issue prior to installing Vagrant. 
>>>>
>>>> If I bring up a VM, I am able to RDP into a guest from outside via 
>>>> IP:ForwardedPort. Is there a way to force any port forwarding configs to 
>>>> be 
>>>> flushed out if a Vagrant Destroy is not doing this?
>>>>
>>>

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