SmtpClientDiag

1.3.0.1

InternalSmtpClient.psm1

                                using module .\Logger.psm1

class InternalSmtpClient {

    hidden [System.Net.Sockets.TcpClient]$TcpClient

    hidden [int]$TimeoutMs

    hidden [System.IO.StreamReader]$Reader

    hidden [System.IO.StreamWriter]$Writer

    hidden [string[]]$SessionCapabilities

    hidden [string]$LastSmtpResponse

    hidden [Logger]$Logger

    [int]$TimeoutSec = 60

    [int]$ResponseCode = -1

    InternalSmtpClient ([Logger]$logger) {

        $this.Logger = $logger

    }

    [void] Connect([string]$smtpServer, [int]$port, [bool]$useSsl, [bool]$acceptUntrustedCertificates, [System.Security.Cryptography.X509Certificates.X509Certificate]$clientCertificate, [System.Security.Authentication.SslProtocols]$enabledSslProtocols) {

        [bool]$useClientCert = $false

        $this.TimeoutMs = $this.TimeoutSec * 1000

        if ($null -ne $clientCertificate) {

            $useClientCert = $true

        }

        $this.logger.LogMessage("# Tcp Client Timeout Settings", "Information", $true, $true)

        $this.logger.LogMessage("TcpClientReceiveTimeOut: $($this.TimeoutSec)s", "Information", $true, $true)

        $this.logger.LogMessage("TcpClientSendTimeOut: $($this.TimeoutSec)s", "Information", $true, $true)

        $this.logger.LogMessage("", "Information", $true, $true)

        $this.logger.LogMessage("[Connecting to $SmtpServer" + ":$Port]", "Information", "Yellow", $false, $true)

        $this.TcpClient = New-Object System.Net.Sockets.TcpClient

        $this.TcpClient.ReceiveTimeout = $this.TimeoutMs

        $this.TcpClient.SendTimeout = $this.TimeoutMs

        $result = $this.TcpClient.BeginConnect($SmtpServer, $Port, $null, $null)

        $result.AsyncWaitHandle.WaitOne($this.TimeoutMs) | Out-Null

        $this.TcpClient.EndConnect($result)

        if (-not $this.TcpClient.Connected) {

            # If not connected exception *should* be thrown in EndConnect()

            $this.Logger.LogError("Connection to remote host $($SmtpServer + ":$Port") failed!")

        }

        $this.Logger.LogMessage("[Connected]", "Information", "Green", $false, $true)

        $this.Reader = New-Object System.IO.StreamReader::($this.TcpClient.GetStream(), [System.Text.Encoding]::ASCII)

        $this.Writer = New-Object System.IO.StreamWriter::($this.TcpClient.GetStream(), [System.Text.Encoding]::ASCII)

        $this.ReadResponse()

        $this.SendEhlo()

        if ($useSsl) {

            $this.Logger.LogMessage("Starting TLS...", "Verbose", $false, $true)

            if ($this.SessionCapabilities.Contains("STARTTLS")) {

                $this.SmtpCmd("STARTTLS")

                if ($this.ResponseCode -eq 220) {

                    $this.Logger.LogMessage("* Starting TLS negotiation")

                    if ($AcceptUntrustedCertificates) {

                        $this.Logger.LogMessage("Ignoring certificate validation results.", "Verbose", $false, $true)

                        $sslstream = New-Object System.Net.Security.SslStream::($this.TcpClient.GetStream(), $false, ({ $true } -as [Net.Security.RemoteCertificateValidationCallback]))

                    }

                    else {

                        $sslstream = New-Object System.Net.Security.SslStream::($this.TcpClient.GetStream())

                    }

                    if ($useClientCert) {

                        $certcol = New-Object System.Security.Cryptography.X509Certificates.X509CertificateCollection

                        $certcol.Add($clientCertificate)

                        $sslstream.AuthenticateAsClient($SmtpServer, $certcol, $enabledSslProtocols, $true)

                    }

                    else {

                        $sslstream.AuthenticateAsClient($SmtpServer, $null, $enabledSslProtocols, $true)

                    }

                    $this.Writer = New-Object System.IO.StreamWriter::($sslstream, [System.Text.Encoding]::ASCII)

                    $this.Reader = New-Object System.IO.StreamReader::($sslstream, [System.Text.Encoding]::ASCII)

                    $this.Logger.LogMessage("* TLS negotiation completed. IgnoreCertValidation:$AcceptUntrustedCertificates CipherAlgorithm:$($sslstream.CipherAlgorithm) HashAlgorithm:$($sslstream.HashAlgorithm) TlsVersion:$($sslstream.SslProtocol)")

                    $this.Logger.LogMessage("* RemoteCertificate: '<S>$($sslstream.RemoteCertificate.Subject)<I>$($sslstream.RemoteCertificate.Issuer)' NotBefore:$($sslstream.RemoteCertificate.GetEffectiveDateString()) NotAfter:$($sslstream.RemoteCertificate.GetExpirationDateString())")

                    if ($useClientCert) {

                        $this.Logger.LogMessage("* ClientCertificate: '<S>$($sslstream.LocalCertificate.Subject)<I>$($sslstream.LocalCertificate.Issuer)' NotBefore:$($sslstream.LocalCertificate.GetEffectiveDateString()) NotAfter:$($sslstream.LocalCertificate.GetExpirationDateString())")

                    }

                    # Warn if using unsupported versions of TLS

                    # Intentionally not setting TLS to 1.2 or greater to expose default TLS behavior

                    if ($sslstream.SslProtocol -eq "Tls" -or $sslstream.SslProtocol -eq "Tls11") {

                        Write-Warning "TLS version is either 1.0 or 1.1. Consider enabling TLS 1.2 or greater."

                    }

                    $rawCert = "`n-----BEGIN CERTIFICATE-----"

                    $rawCert += "`n" + [Convert]::ToBase64String($sslstream.RemoteCertificate.GetRawCertData(), [System.Base64FormattingOptions]::InsertLineBreaks)

                    $rawCert += "`n-----END CERTIFICATE----- "

                    $this.Logger.LogMessage("Remote Certificate:", "Verbose", $false, $true)

                    $this.Logger.LogMessage($rawCert, "Verbose", $false, $true)

                    # Rediscover session capabilities

                    $this.SendEhlo()

                }

                else {

                    throw "Failed to start tls session with remote host."

                }

            }

            # STARTTLS verb not found

            else {

                throw "Session capabilities do not support STARTTLS."

            }

        }

    }

    [void] ReadResponse() {

        $this.ResponseCode = - 1

        $resp = @()

        # Bail if not connected

        if (-not $this.TcpClient.Connected) {

            throw "Client is not connected."

        }

        $line = $this.Reader.ReadLine()

        if ([System.String]::IsNullOrEmpty($line)) {

            return

        }

        $resp += $line

        # Parse response code

        $this.ResponseCode = [System.Int32]::Parse($line.Substring(0, 3))

        # Read all lines

        while ($this.Reader.Peek() -gt 0) {

            Write-Debug "StreamReader: Reading more lines..."

            $line = $this.Reader.ReadLine()

            if ([System.String]::IsNullOrEmpty($line)) {

                Write-Error -Message "End of stream."

            }

            # If more lines, truncate response code

            $resp += $line.Substring(4)

        }

        $this.LastSmtpResponse = $resp -join ','

        $this.Logger.LogMessage("< " + $resp)

    }

    [void] SendEhlo() {

        $this.SmtpCmd("EHLO " + ([System.Environment]::MachineName))

        if ($this.ResponseCode -ne 250) {

            throw "Unexpected response on EHLO command. Response Code:$($this.ResponseCode)"

        }

        $lines = $this.LastSmtpResponse.Split(',') | Where-Object { ($_) -and ($_ -notcontains "250") }

        $this.SessionCapabilities = $lines

    }

    [void] SmtpCmd([string]$command) {

        $this.SmtpCmd($command, $false)

    }

    [void] SmtpCmd([string]$command, [bool]$redactCmd) {

        if ($redactCmd) {

            $this.Logger.LogMessage("Sending command: *REDACTED*", "Verbose", $false, $true)

            $this.Logger.LogMessage("> *REDACTED*")

        }

        else {

            $this.Logger.LogMessage("Sending command: $command", "Verbose", $false, $true)

            $this.Logger.LogMessage("> " + $command)

        }

        $this.Writer.WriteLine($command)

        $this.Writer.Flush()

        if (($command -ne "QUIT") -and (!$command.StartsWith("BDAT"))) {

            $this.ReadResponse()

        }

    }

    [bool] ContainsCapability([string] $c) {

        foreach ($cap in $this.SessionCapabilities) {

            if ($cap.ToLower().Contains($c.ToLower())) {

                return $true

            }

        }

        return $false

    }

    [bool] AuthLogin([pscredential]$Credential) {

        if ($this.ContainsCapability("AUTH LOGIN")) {

            $this.SmtpCmd("AUTH LOGIN")

            if ($this.ResponseCode -eq 334) {

                $message = [System.Text.Encoding]::ASCII.GetString([System.Convert]::FromBase64String($this.LastSmtpResponse.Substring(4))).ToLower()

                if ($message -eq "username:") {

                    $this.SmtpCmd([System.Convert]::ToBase64String([System.Text.Encoding]::ASCII.GetBytes($Credential.UserName)))

                }

                # Decode the response

                $message = [System.Text.Encoding]::ASCII.GetString([System.Convert]::FromBase64String($this.LastSmtpResponse.Substring(4))).ToLower()

                # If username accepted continue

                if (($this.ResponseCode -eq 334) -and ($message -eq "password:")) {

                    $this.SmtpCmd([System.Convert]::ToBase64String([System.Text.Encoding]::ASCII.GetBytes($Credential.GetNetworkCredential().Password)), $true)

                }

                else {

                    $this.Logger.LogError("SMTP Authentication Failed. Invalid user name.")

                    return $false

                }

                if ($this.ResponseCode -eq 535 -and $($this.LastSmtpResponse.Substring(4)).StartsWith("5.7.139")) {

                    $this.Logger.LogError("SMTP Authentication Failed. Basic authentication disabled or blocked by policy.")

                    return $false

                }

                if ($this.ResponseCode -eq 421) {

                    $this.Logger.LogError("SMTP Authentication Failed. Check your TLS version is at least 1.2.")

                    return $false

                }

                if ($this.ResponseCode -ne 235) {

                    $this.Logger.LogError("SMTP Authentication Failed. Check user name and password.")

                    return $false

                }

                return $true

            }

            else {

                $this.Logger.LogError("Unexpected response code on AUTH LOGIN.")

            }

        }

        else {

            $this.Logger.LogError("Session capabilities do not support AUTH LOGIN")

        }

        return $false

    }

    [bool] XOAUTH2Login([string]$userName, [string]$token) {

        if ([System.String]::IsNullOrEmpty($token)) {

            $this.Logger.LogError("AccessToken is null or empty")

            return $false

        }

        # Build the auth blob

        $authBlob = "user=" + $UserName + "$([char]0x01)auth=Bearer " + $token + "$([char]0x01)$([char]0x01)"

        if ($this.ContainsCapability("XOAUTH2")) {

            $this.SmtpCmd("AUTH XOAUTH2")

            if ($this.ResponseCode -eq 334) {

                $this.SmtpCmd([System.Convert]::ToBase64String([System.Text.Encoding]::ASCII.GetBytes($authBlob)))

                if ($this.ResponseCode -eq 421) {

                    $this.Logger.LogError("SMTP Authentication Failed. Check your TLS version is at least 1.2.")

                    return $false

                }

                if ($this.ResponseCode -eq 235) {

                    return $true

                }

                else {

                    $this.Logger.LogError("SMTP Authentication Failed. Check your OAUTH token is valid.")

                    return $false

                }

            }

            else {

                $this.Logger.LogError("Unexpected response code on AUTH XOAUTH2.")

                return $false

            }

        }

        else {

            $this.Logger.LogError("Session capabilities do not support AUTH XOAUTH2.")

            return $false

        }

    }

    [void] SendMail([string]$From, [string]$To) {

        $this.SmtpCmd("MAIL FROM: <$From>")

        if ($this.ResponseCode -ne 250) {

            $this.Logger.LogError("Unexpected response code on MAIL FROM command.")

            $this.SmtpCmd("QUIT")

            return

        }

        $this.SmtpCmd("RCPT TO: <$To>")

        if ($this.ResponseCode -ne 250) {

            $this.Logger.LogError("Unexpected response code on RCPT TO command.")

            $this.SmtpCmd("QUIT")

            return

        }

        $message = "From: `"$From`" <$From>"

        $message += "`nTo: `"$To`" <$To>"

        $message += "`nSubject: SMTP Client Submission Test"

        $message += "`nContent-Type: text/plain"

        $message += "`n"

        $message += "`nThis is a test message."

        # Script does not check for chuncking capability as it is not meant to support all MTAs

        # BDAT is preferred over DATA command

        $byteCount = [System.Text.Encoding]::ASCII.GetByteCount($message)

        $command = "BDAT $byteCount LAST"

        $this.SmtpCmd($command)

        $this.Logger.LogMessage("Writing message to stream...", "Verbose", $false, $true)

        $this.Writer.Write($message)

        $this.Writer.Flush()

        $this.ReadResponse()

        if ($this.ResponseCode -eq 430 -and $($this.LastSmtpResponse.Substring(4)).StartsWith("4.2.0 STOREDRV; mailbox logon failure;")) {

            $this.Logger.LogError("Failed to submit message. Verify that the authenticated user or application has the correct permission to logon to the mailbox.")

        }

        elseif ($this.ResponseCode -ne 250) {

            $this.Logger.LogError("Failed to submit message.")

        }

        $this.SmtpCmd("QUIT")

    }

    [void] DisposeResources() {

        if ($this.Writer) {

            $this.Writer.Dispose()

        }

        if ($this.Reader) {

            $this.Reader.Dispose()

        }

        if ($this.TcpClient) {

            $this.TcpClient.Dispose()

        }

    }

}

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