CertifyTheWeb to set RDGW certificate.

awesomesupercoolscriptquiteretarded.ps1

param($result)

Import-Module RemoteDesktop

# For some reason this is needed on Swedish operating systems to get the PS modules working with CertifyTheWeb
if (-Not (Test-Path "C:\Windows\System32\WindowsPowerShell\v1.0\Modules\RemoteDesktop\sv-SE"))
{
    Copy-Item -Recurse "C:\Windows\System32\WindowsPowerShell\v1.0\Modules\RemoteDesktop\en" "C:\Windows\System32\WindowsPowerShell\v1.0\Modules\RemoteDesktop\sv-SE"
}

# Because Microsoft software is very non-deterministic things usually just work out if you insist hard enough.
For ($i=0; $i -le 10; $i++)
{
    try
    {
        if (Get-Command Set-RDCertificate)
        {
            if ((Get-RDCertificate -Role RDGateway).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
                Set-RDCertificate -Role RDGateway -ImportPath $result.ManagedItem.CertificatePath -Force -ErrorAction Stop
            }
            if ((Get-RDCertificate -Role RDWebAccess).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
                Set-RDCertificate -Role RDWebAccess -ImportPath $result.ManagedItem.CertificatePath -Force -ErrorAction Stop
            }
            if ((Get-RDCertificate -Role RDPublishing).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
                Set-RDCertificate -Role RDPublishing -ImportPath $result.ManagedItem.CertificatePath -Force -ErrorAction Stop
            }
            if ((Get-RDCertificate -Role RDRedirector).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
                Set-RDCertificate -Role RDRedirector -ImportPath $result.ManagedItem.CertificatePath -Force -ErrorAction Stop
            }
        }
        else
        {
            wmic /namespace:\\root\cimv2\TerminalServices PATH Win32_TSGeneralSetting Set SSLCertificateSHA1Hash="$($result.ManagedItem.CertificateThumbprintHash)"
            Set-Item -Path RDS:\GatewayServer\SSLCertificate\Thumbprint -Value $result.ManagedItem.CertificateThumbprintHash -ErrorAction Stop

        }
        $i += 1337
    }
    catch {
    }
}

# Yes if multiple fail we'll only get one error, deal with it.
if ((Get-RDCertificate -Role RDGateway).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
    throw "Failed to set RDGateway"
}
if ((Get-RDCertificate -Role RDWebAccess).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
    throw "Failed to set RDWebAccess"
}
if ((Get-RDCertificate -Role RDPublishing).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
    throw "Failed to set RDPublishing"
}
if ((Get-RDCertificate -Role RDRedirector).Thumbprint -ne $result.ManagedItem.CertificateThumbprintHash) {
    throw "Failed to set RDRedirector"
}

Start-Sleep -Seconds 30
# This has proven to be required sometimes, again because this is all 100% deterministic
Restart-Service TSGateway -Force