After some more research I found : 
https://github.com/mitchellh/vagrant-aws/issues/180
https://github.com/mitchellh/vagrant-aws/issues/247

Does that mean it is not possible yet? Any work around?

Thanks !

On Monday, September 22, 2014 7:52:51 PM UTC-7, Shawn McCarthy wrote:
>
> I have been trying to start a Windows guest in AWS EC2, and can't figure 
> out how to get the password in the Vagrantfile.
>
> With Linux, I see this is used :
>     override.ssh.private_key_path = "test-ec2-1.pem"
>
> But this doesn't seem to work for Windows guests in AWS EC2. I think it is 
> because it uses WinRm, not SSH. How can I get the password passed into the 
> Vagrantfile ?
>
> I see messages like this when I do : vagrant up --provider=aws --debug :
>
> DEBUG winrmshell: initializing WinRMShell
> DEBUG winrmshell: powershell executing:
> hostname
> if ($?) { exit 0 } else { if($LASTEXITCODE) { exit $LASTEXITCODE } else { 
> exit 1 } }
>  INFO winrmshell: Attempting to connect to WinRM...
>  INFO winrmshell:   - Host: xxx.xxx.xxx.xxx (masked)
>  INFO winrmshell:   - Port: 5985
>  INFO winrmshell:   - Username: Administrator
>  INFO retryable: Retryable exception raised: 
> #<WinRM::WinRMHTTPTransportError: Bad HTTP response returned from server 
> (401).>
>
> My Vagrantfile:
>
> # -*- mode: ruby -*-
> # vi: set ft=ruby :
>
> Vagrant.configure("2") do |config|
>   config.vm.box = "dummy"
>   config.vm.box_url = "
> https://github.com/mitchellh/vagrant-aws/raw/master/dummy.box";
>   config.vm.communicator = "winrm"
>   config.winrm.username = "Administrator"
>
>   config.vm.provider :aws do |aws, override|
>     aws.access_key_id = ENV['AWS_ACCESS_KEY_ID']
>     aws.secret_access_key = ENV['AWS_SECRET_ACCESS_KEY']
>     aws.keypair_name = ENV['AWS_KEYPAIR_NAME']
>     aws.ami = "ami-e189c8d1"
>     aws.security_groups = [ 'vagrant' ]
>     aws.region = "us-west-2"
>     aws.instance_type = "t2.micro"
>   end
> end
>
> To get the password, I use the AWS console and Right Click a running 
> Instance and click Get Password. Than I need to give it my .pem file and it 
> gives me the cryptic password I can use to RDP into the instance. I would 
> like a way to use the .pem file in my Vagrantfile. Or maybe there is 
> another way?
>
> Thank you!
>

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