MassMailer/tools/test-smtp-capabilities.ps1

param(
    [string]$ConfigPath = (Join-Path (Split-Path -Parent $PSScriptRoot) 'config.ini')
)

$ErrorActionPreference = 'Stop'
$settings = @{}
foreach ($line in Get-Content -LiteralPath $ConfigPath -Encoding UTF8) {
    if ($line -match '^\s*([A-Z_]+)\s*=\s*(.*?)\s*$') {
        $settings[$matches[1]] = $matches[2]
    }
}
$smtpHost = $settings['SMTP_HOST']
$smtpPort = 0
if ([string]::IsNullOrWhiteSpace($smtpHost) -or
    -not [int]::TryParse($settings['SMTP_PORT'], [ref]$smtpPort) -or
    $smtpPort -lt 1 -or $smtpPort -gt 65535) {
    throw 'Valid SMTP_HOST and SMTP_PORT are required in the config file'
}

function Read-Reply($reader) {
    $lines = New-Object 'System.Collections.Generic.List[string]'
    do {
        $line = $reader.ReadLine()
        if ($null -eq $line -or $line -notmatch '^\d{3}[- ]') {
            throw "Invalid or incomplete SMTP reply: $line"
        }
        $lines.Add($line)
    } while ($line.Substring(3, 1) -eq '-')
    return ,$lines.ToArray()
}

$client = New-Object System.Net.Sockets.TcpClient
try {
    $connect = $client.BeginConnect($smtpHost, $smtpPort, $null, $null)
    if (-not $connect.AsyncWaitHandle.WaitOne(10000)) { throw 'SMTP connection timed out' }
    $client.EndConnect($connect)
    $client.ReceiveTimeout = 10000
    $client.SendTimeout = 10000
    $stream = $client.GetStream()
    $reader = New-Object System.IO.StreamReader($stream, [System.Text.Encoding]::ASCII)
    $writer = New-Object System.IO.StreamWriter($stream, [System.Text.Encoding]::ASCII)
    $writer.NewLine = "`r`n"
    $writer.AutoFlush = $true

    $greeting = Read-Reply $reader
    if (-not $greeting[-1].StartsWith('220')) { throw "SMTP greeting rejected: $($greeting[-1])" }
    $writer.WriteLine('EHLO localhost')
    $ehlo = Read-Reply $reader
    if (-not $ehlo[-1].StartsWith('250')) { throw "EHLO rejected: $($ehlo[-1])" }
    if (-not ($ehlo | Where-Object { $_ -match '^250[- ]STARTTLS(?:\s|$)' })) {
        throw 'Server did not advertise STARTTLS'
    }
    $writer.WriteLine('STARTTLS')
    $startTls = Read-Reply $reader
    if (-not $startTls[-1].StartsWith('220')) { throw "STARTTLS rejected: $($startTls[-1])" }

    $secureStream = New-Object System.Net.Security.SslStream($stream, $false)
    $secureStream.AuthenticateAsClient($smtpHost)
    if (-not $secureStream.IsAuthenticated -or -not $secureStream.IsEncrypted) {
        throw 'TLS negotiation did not establish an encrypted session'
    }
    Write-Output "SMTP STARTTLS OK: $smtpHost`:$smtpPort ($($secureStream.SslProtocol))"
    $secureStream.Close()
}
finally {
    $client.Close()
}