SmtpClientDiag

1.3.0.1

Test-SmtpClientCertificate.psm1

                                <#

 .Synopsis

  Diagnostic module for testing SMTP connector attribution.

 .Description

  Diagnostic module for testing SMTP connector attribution.

 .Parameter From

  The From SMTP email address.

 .Parameter To

  The To SMTP email address.

 .Parameter SmtpServer

  The remote SMTP server that will be accepting mail.

 .Parameter CertificateThumbprint

  The client certificate thumbprint to use for authentication.

 .Parameter TlsVersion

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

 .Parameter LogPath

  The path to the log file.

 .Example

   # Submit mail with client certificate

   Test-SmtpClientCertificate -From <FromAddress> -To <RecipientAddress> -SmtpServer your-domain.mail.protection.outlook.com -CertificateThumbprint <thumbprint>

#>

using module .\InternalSmtpClient.psm1

using module .\Utils.psm1

using module .\Logger.psm1

function Test-SmtpClientCertificate() {

    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 = $true)]

        [string] $SmtpServer,

        [Parameter(Mandatory = $true)]

        [string] $CertificateThumbprint,

        [Parameter(Mandatory = $false)]

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

        [string] $TlsVersion,

        [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

    )

    # Check version

    CheckVersionAndWarn

    # Set Tls version

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

    # Check if running as administrator

    # Elevation is needed to gain access to the certificate private key

    if ((New-Object Security.Principal.WindowsPrincipal([Security.Principal.WindowsIdentity]::GetCurrent())).IsInRole([Security.Principal.WindowsBuiltInRole]::Administrator) -eq $false) {

        Write-Warning "Missing elevation! Elevation may be required to gain access to the certificate's private key."

    }

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

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

    [System.Security.Cryptography.X509Certificates.X509Certificate2]$clientCertificate = $null

    try {

        $clientCertificate = RetrieveCertificateFromCertStore($CertificateThumbprint)

        $smtpClient.Connect($SmtpServer, 25, $true, $false, $clientCertificate, $enabledSslProtocols)

        $smtpClient.SendMail($From, $To)

    }

    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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