Windows on AWS with Vagrant

user_data.txt

<powershell>

# Disable Complex Passwords
# Reference: http://vlasenko.org/2011/04/27/removing-password-complexity-requirements-from-windows-server-2008-core/
$seccfg = [IO.Path]::GetTempFileName()
secedit /export /cfg $seccfg
(Get-Content $seccfg) | Foreach-Object {$_ -replace "PasswordComplexity\s*=\s*1", "PasswordComplexity=0"} | Set-Content $seccfg
secedit /configure /db $env:windir\security\new.sdb /cfg $seccfg /areas SECURITYPOLICY
del $seccfg
Write-Host "Complex Passwords have been disabled." -ForegroundColor Green

$ComputerName = $env:COMPUTERNAME
$user = [adsi]"WinNT://$ComputerName/Administrator,user"
$user.setpassword("VagrantRocks")

# WinRM
write-output "Setting up WinRM"
write-host "(host) setting up WinRM"

cmd.exe /c winrm quickconfig -q
cmd.exe /c winrm quickconfig '-transport:http'
cmd.exe /c winrm set "winrm/config" '@{MaxTimeoutms="1800000"}'
cmd.exe /c winrm set "winrm/config/winrs" '@{MaxMemoryPerShellMB="1024"}'
cmd.exe /c winrm set "winrm/config/service" '@{AllowUnencrypted="true"}'
cmd.exe /c winrm set "winrm/config/client" '@{AllowUnencrypted="true"}'
cmd.exe /c winrm set "winrm/config/service/auth" '@{Basic="true"}'
cmd.exe /c winrm set "winrm/config/client/auth" '@{Basic="true"}'
cmd.exe /c winrm set "winrm/config/service/auth" '@{CredSSP="true"}'
cmd.exe /c winrm set "winrm/config/listener?Address=*+Transport=HTTP" '@{Port="5985"}'
cmd.exe /c netsh advfirewall firewall set rule group="remote administration" new enable=yes
cmd.exe /c netsh firewall add portopening TCP 5985 "Port 5985"
cmd.exe /c net stop winrm
cmd.exe /c sc config winrm start= auto
cmd.exe /c net start winrm

# Disable Internet Explorer Security
# http://stackoverflow.com/a/9368555/2067999
$AdminKey = "HKLM:\SOFTWARE\Microsoft\Active Setup\Installed Components\{A509B1A7-37EF-4b3f-8CFC-4F3A74704073}"
$UserKey = "HKLM:\SOFTWARE\Microsoft\Active Setup\Installed Components\{A509B1A8-37EF-4b3f-8CFC-4F3A74704073}"
Set-ItemProperty -Path $AdminKey -Name "IsInstalled" -Value 0
Set-ItemProperty -Path $UserKey -Name "IsInstalled" -Value 0

# Do not combine taskbar buttons
# http://superuser.com/a/741155
Set-ItemProperty -Path HKCU:\Software\Microsoft\Windows\CurrentVersion\Explorer\Advanced -Name TaskbarGlomLevel -Value 1
Get-Process -Name explorer | Stop-Process

(iex ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1')))>$null 2>&1
choco install GoogleChrome -y
choco install babun -y

</powershell>

Vagrantfile

require 'inifile'
require 'date'

Vagrant.configure("2") do |config|
  config.vm.box = "dummy"

  config.vm.guest = "windows"
  config.vm.boot_timeout = 600

  config.vm.provider :aws do |aws, override|
    # https://gist.github.com/amosshapira/e043ef116bfdfe92e3cd
    aws_credentials = IniFile.load(File.expand_path('~/.aws/credentials'))
    aws.access_key_id = aws_credentials['default']['aws_access_key_id']
    aws.secret_access_key = aws_credentials['default']['aws_secret_access_key']

    aws.region = 'eu-west-1'

    aws.keypair_name = "keypair" # << FIXME
    aws.ami = "ami-c343ecb0" # Microsoft Windows Server 2012 Base
    aws.instance_type = "t2.micro"
    aws.terminate_on_shutdown = true
    aws.security_groups = ["sg-123"] # << FIXME
    aws.subnet_id = "subnet-123" # << FIXME
    aws.associate_public_ip = true

    # aws.spot_instance = true
    # aws.spot_max_price = 0.0155
    # aws.spot_valid_until = DateTime.now + (3.0/24)
    aws.tags = {
      'Name' => 'vagrant-test'
    }

    aws.user_data = File.read("user_data.txt")

    override.vm.communicator = "winrm"
    override.winrm.username = "Administrator"
    override.winrm.password = "VagrantRocks"

    override.vm.synced_folder ".", "/vagrant", disabled: true
  end
end

Hi there,

I have been trying to use the above code but I seem to be running into issues.
I am successfully able to create the Windows EC2 instance but then it eventually gets stuck when it says "waiting for SSH to become available"

Here is the output I get from Powershell, would know what I am doing wrong?

PS C:\qmi\qmi-scenarios\deanscenario> Vagrant up --provider=aws
Bringing machine 'default' up with 'aws' provider...
==> default: Preparing SMB shared folders...
default: You will be asked for the username and password to use for the SMB
default: folders shortly. Please use the proper username/password of your
default: account.
default:
default: Username:
default: Password (will be hidden):
==> default: Warning! The AWS provider doesn't support any of the Vagrant
==> default: high-level network configurations (config.vm.network). They
==> default: will be silently ignored.
==> default: Launching an instance with the following settings...
==> default: -- Type: t2.micro
==> default: -- AMI: ami-9bb358fc
==> default: -- Region: eu-west-2
==> default: -- Keypair: <keypair_name>
==> default: -- User Data: yes
==> default: -- User Data:
==> default:
==> default: # Disable Complex Passwords
==> default: # Reference: http://vlasenko.org/2011/04/27/removing-password-complexity-requirements-from-windows-server-2008-core/
==> default: $seccfg = [IO.Path]::GetTempFileName()
==> default: secedit /export /cfg $seccfg
==> default: (Get-Content $seccfg) | Foreach-Object {$_ -replace "PasswordComplexity\s*=\s1", "PasswordComplexity=0"} | Set-Content $seccfg
==> default: secedit /configure /db $env:windir\security\new.sdb /cfg $seccfg /areas SECURITYPOLICY
==> default: del $seccfg
==> default: Write-Host "Complex Passwords have been disabled." -ForegroundColor Green
==> default:
==> default: $ComputerName = $env:COMPUTERNAME
==> default: $user = [adsi]"WinNT://$ComputerName/Administrator,user"
==> default: $user.setpassword("VagrantRocks")
==> default:
==> default: # WinRM
==> default: write-output "Setting up WinRM"
==> default: write-host "(host) setting up WinRM"
==> default:
==> default: cmd.exe /c winrm quickconfig -q
==> default: cmd.exe /c winrm quickconfig '-transport:http'
==> default: cmd.exe /c winrm set "winrm/config" '@{MaxTimeoutms="1800000"}'
==> default: cmd.exe /c winrm set "winrm/config/winrs" '@{MaxMemoryPerShellMB="1024"}'
==> default: cmd.exe /c winrm set "winrm/config/service" '@{AllowUnencrypted="true"}'
==> default: cmd.exe /c winrm set "winrm/config/client" '@{AllowUnencrypted="true"}'
==> default: cmd.exe /c winrm set "winrm/config/service/auth" '@{Basic="true"}'
==> default: cmd.exe /c winrm set "winrm/config/client/auth" '@{Basic="true"}'
==> default: cmd.exe /c winrm set "winrm/config/service/auth" '@{CredSSP="true"}'
==> default: cmd.exe /c winrm set "winrm/config/listener?Address=+Transport=HTTP" '@{Port="5985"}'
==> default: cmd.exe /c netsh advfirewall firewall set rule group="remote administration" new enable=yes
==> default: cmd.exe /c netsh firewall add portopening TCP 5985 "Port 5985"
==> default: cmd.exe /c net stop winrm
==> default: cmd.exe /c sc config winrm start= auto
==> default: cmd.exe /c net start winrm
==> default:
==> default: # Disable Internet Explorer Security
==> default: # http://stackoverflow.com/a/9368555/2067999
==> default: $AdminKey = "HKLM:\SOFTWARE\Microsoft\Active Setup\Installed Components{A509B1A7-37EF-4b3f-8CFC-4F3A74704073}"
==> default: $UserKey = "HKLM:\SOFTWARE\Microsoft\Active Setup\Installed Components{A509B1A8-37EF-4b3f-8CFC-4F3A74704073}"
==> default: Set-ItemProperty -Path $AdminKey -Name "IsInstalled" -Value 0
==> default: Set-ItemProperty -Path $UserKey -Name "IsInstalled" -Value 0
==> default:
==> default: # Do not combine taskbar buttons
==> default: # http://superuser.com/a/741155
==> default: Set-ItemProperty -Path HKCU:\Software\Microsoft\Windows\CurrentVersion\Explorer\Advanced -Name TaskbarGlomLevel -Value 1
==> default: Get-Process -Name explorer | Stop-Process
==> default:
==> default: (iex ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1')))>$null 2>&1
==> default: choco install GoogleChrome -y
==> default: choco install babun -y
==> default:
==> default:
==> default: -- Block Device Mapping: []
==> default: -- Terminate On Shutdown: true
==> default: -- Monitoring: false
==> default: -- EBS optimized: false
==> default: -- Source Destination check:
==> default: -- Assigning a public IP address in a VPC: false
==> default: -- VPC tenancy specification: default
==> default: Waiting for instance to become "ready"...
==> default: Waiting for SSH to become available...