Recipe for getting a prompt on a stock Windows EC2 instance

recipe.txt

In userdata on the target:

<powershell>
$admin = [adsi]("WinNT://./administrator, user")
$admin.PSBase.Invoke("SetPassword", "SufficientlyC0mplexPasswordHere!")
Invoke-Expression ((New-Object System.Net.Webclient).DownloadString('https://gist.githubusercontent.com/tomfanning/19a983ad793e63d68117bd90bd57e02b/raw/8508a56fd5eb0456e2aa34a278cb7e6fbafe9dd8/configure-windows-remoting-ec2.ps1'))
</powershell>

Also ensure a security group is applied which opens port 5986.

Start the VM. Can take a few minutes for the script to sort itself out.

Then from a bastion host:

$hostName="ec2-1-2-3-4.eu-west-2.compute.amazonaws.com" # 
$winrmPort = "5986"
$password = ConvertTo-SecureString "SufficientlyC0mplexPasswordHere!" -AsPlainText -Force
$cred= New-Object System.Management.Automation.PSCredential ("administrator", $password )
$soptions = New-PSSessionOption -SkipCACheck
Enter-PSSession -ComputerName $hostName -Port $winrmPort -Credential $cred -SessionOption $soptions -UseSSL

ta da! prompt.

Now need to get it running on standard HTTPS port, through authenticated proxy...