SmtpClientDiag

1.3.0.0

Test-SmtpClientSubmission.psm1

                                <#

 .Synopsis

  Diagnostic module for testing SMTP client submission.

 .Description

  Diagnostic module for testing SMTP client submission. This function supports Basic (AUTH LOGIN) and Modern (XOAUTH2) authentication.

 .Parameter From

  The From SMTP email address.

 .Parameter To

  The To SMTP email address.

 .Parameter UseSsl

  Enables the use of TLS if supported by the remote MTA.

 .Parameter AcceptUntrustedCertificates

  Disables certificate validation

 .Parameter TlsVersion

  Specify the Tls version. If none specified the default OS version is used. Accepted values are tls, tls11, tls12, tls13.

 .Parameter SmtpServer

  The remote SMTP server that will be accepting mail.

 .Parameter Port

  The remote network port number. By default the port is 587 if not specified.

 .Parameter Credential

  User credentials for basic authentication.

 .Parameter AccessToken

  Optional parameter to consume an external token.

 .Parameter UserName

  Username of the account for modern authentication. Required to build the auth blob.

 .Parameter ClientId

  Azure Application Client Id.

 .Parameter TenantId

  Azure / Office 365 Tenant Id.

 .Parameter TimeoutSec

  Optional parameter to force a timeout value other than the default of 10 seconds.

 .Parameter Force

  Optional parameter to force mail submission.

 .Example

   # Submit mail without credentials.

   Test-SmtpClientSubmission -From <FromAddress> -To <RecipientAddress> -UseSsl -SmtpServer smtp.office365.com -Port 25 -Force

 .Example

   # Submit mail using legacy authentication.

   Test-SmtpClientSubmission -From <FromAddress> -To <RecipientAddress> -UseSsl -SmtpServer smtp.office365.com -Port 587 -Credential <PSCredential>

 .Example

   # Submit mail using modern authentication.

   Test-SmtpClientSubmission -From <FromAddress> -To <RecipientAddress> -UseSsl -SmtpServer smtp.office365.com -Port 587 -UserName <MailboxSmtp> -ClientId 9954180a-16f4-4683-aaaaaaaaaaaa -TenantId 1da8c747-60dd-4404-8418-aaaaaaaaaaaa

#>

using module .\InternalSmtpClient.psm1

using module .\Utils.psm1

using module .\Logger.psm1

function Test-SmtpClientSubmission() {

    [CmdletBinding(DefaultParameterSetName = "Default")]

    param(

        [Parameter(Mandatory = $true)]

        [ValidateScript({

                try {

                    $null = [mailaddress]$_

                    return $true

                }

                catch {

                    throw "The specified string is not in the form required for an e-mail address."

                }

            })]

        [string] $From,

        [Parameter(Mandatory = $true)]

        [ValidateScript({

                try {

                    $null = [mailaddress]$_

                    return $true

                }

                catch {

                    throw "The specified string is not in the form required for an e-mail address."

                }

            })]

        [string] $To,

        [Parameter(Mandatory = $false)]

        [switch] $UseSsl,

        [Parameter(Mandatory = $false)]

        [switch] $AcceptUntrustedCertificates,

        [Parameter(Mandatory = $false)]

        [ValidateSet("tls", "tls11", "tls12", "tls13", IgnoreCase = $true)]

        [string] $TlsVersion,

        [Parameter(Mandatory = $true)]

        [string] $SmtpServer,

        [Parameter(Mandatory = $false)]

        [int] $Port = 587,

        [Parameter(Mandatory = $true, ParameterSetName = "Default")]

        [Parameter(Mandatory = $false, ParameterSetName = "Force")]

        [pscredential] $Credential,

        [Parameter(Mandatory = $true, ParameterSetName = "UserProvidedToken")]

        [string] $AccessToken,

        [Parameter(Mandatory = $true, ParameterSetName = "UserProvidedToken")]

        [Parameter(Mandatory = $true, ParameterSetName = "OAuth_app")]

        [ValidateScript({

                try {

                    $null = [mailaddress]$_

                    return $true

                }

                catch {

                    throw "The specified string is not in the form required for an e-mail address."

                }

            })]

        [string] $UserName,

        [Parameter(Mandatory = $true, ParameterSetName = "OAuth_app")]

        [ValidateScript({

                [System.Guid]::Parse($_) | Out-Null

                $true

            })]

        [guid] $ClientId,

        [Parameter(Mandatory = $true, ParameterSetName = "OAuth_app")]

        [ValidateScript({

                [System.Guid]::Parse($_) | Out-Null

                $true

            })]

        [guid] $TenantId,

        [Parameter(Mandatory = $false, ParameterSetName = "OAuth_app")]

        [SecureString] $ClientSecret,

        [Parameter(Mandatory = $false)]

        [ValidateScript({

                if (Test-Path $_ -PathType Container) {

                    $true

                }

                else {

                    throw "The location '$_' does not exist. Check the path exist and try again."

                }

            })]

        [string] $LogPath,

        [Parameter(Mandatory = $false)]

        [int] $TimeoutSec,

        [Parameter(Mandatory = $true, ParameterSetName = "Force")]

        [switch] $Force

    )

    # Check version

    CheckVersionAndWarn

    [Logger]$logger = New-Object Logger -ArgumentList $VerbosePreference

    [InternalSmtpClient]$smtpClient = New-Object InternalSmtpClient -ArgumentList $logger

    if ($TimeoutSec -gt 0){

        $smtpClient.TimeoutSec = $TimeoutSec

    }

    # Set Tls version

    [System.Security.Authentication.SslProtocols]$enabledSslProtocols = Get-TlsVersion -TlsVersion $TlsVersion

    # Check if hostname is IP address

    $ipv4Regex = '^(?:25[0-5]|2[0-4]\d|[0-1]?\d{1,2})(?:\.(?:25[0-5]|2[0-4]\d|[0-1]?\d{1,2})){3}$'

    if ($SmtpServer -match $ipv4Regex) {

        $logger.LogMessage("Certificate validation will fail when using an IP address. Consider using a hostname or use -AcceptUntrustedCertificate swtich if testing.", "Warning", $null, $true, $true)

    }

    else {

        # Verbose details for name resolution

        $logger.LogMessage("Resolving hostname to IP addresses...", "Information", $true, $true)

        $logger.LogMessage("# DNS Results", "Information", $true, $true)

        $dns = (Resolve-DnsName -Name $smtpServer -QuickTimeout -ErrorAction SilentlyContinue)

        if ($null -eq $dns) {

            $logger.LogMessage("Failed to resolve hostname to IP addresses.", "Error", $null, $true, $true)

        }

        else {

            $dns | ForEach-Object { if ($null -ne $_.IP4Address) { $logger.LogMessage($_.IP4Address, "Information", $true, $true) } }

            $dns | ForEach-Object { if ($null -ne $_.IP6Address) { $logger.LogMessage($_.IP6Address, "Information", $true, $true) } }

        }

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

    }

    try {

        [bool]$authSuccess = $false

        # Use OAUTH if the client id or access token was supplied

        if (($null -ne $ClientId) -or (-not [System.String]::IsNullOrEmpty($AccessToken))) {

            $logger.LogMessage("[Requesting token]", "Information", "Yellow", $false, $true)

            # Obtain an access token

            Import-Module MSAL.PS -ErrorAction Stop

            $token = Get-SmtpAccessToken -ClientId $ClientId -TenantId $TenantId -ClientSecret $ClientSecret -AccessToken $AccessToken -UserName $UserName -VerbosePref $VerbosePreference

            $smtpClient.Connect($SmtpServer, $Port, $UseSsl, $AcceptUntrustedCertificates, $null, $enabledSslProtocols)

            $authSuccess = $smtpClient.XOAUTH2Login($UserName, $token)

        }

        # Else if no client id check if credentials are available and use legacy auth

        else {

            $smtpClient.Connect($SmtpServer, $Port, $UseSsl, $AcceptUntrustedCertificates, $null, $enabledSslProtocols)

            if ($null -ne $Credential) {

                # Legacy auth

                $authSuccess = $smtpClient.AuthLogin($Credential)

            }

        }

        # Send mail

        if ($authSuccess -eq $true) {

            $logger.LogMessage("Authentication successful", "Verbose", $false, $true)

            $smtpClient.SendMail($From, $To)

        }

        # If force switch true, send mail anyway if auth failed or no creds available

        if ($authSuccess -eq $false -and $Force -eq $true) {

            $logger.LogMessage("Forcing mail submission", "Verbose", $false, $true)

            $smtpClient.SendMail($From, $To)

        }

        elseif ($authSuccess -eq $false) {

            $smtpClient.SmtpCmd("QUIT")

        }

        $logger.LogMessage("Done.", "Verbose", $false, $true)

    }

    catch {

        Write-Error -ErrorRecord $_

        $logger.LogError($_.Exception, $true)

    }

    finally {

        $smtpClient.DisposeResources()

        Write-Debug "Resources disposed."

        $logger.LogMessage("[Disconnected]", "Information", "Red", $false, $true)

        # Write log to file

        $logger.WriteFile($LogPath)

    }

}

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