Send-MailMessage & App Password Doesn’t Work
So today I tried to test SMTP Auth using Powershell
$appPassword = 'my_app_password_here'
$From = "[email protected]"
$To = "[email protected]"
[securestring]$secStringPassword = ConvertTo-SecureString $appPassword -AsPlainText -Force
[pscredential]$msolcred = New-Object System.Management.Automation.PSCredential -ArgumentList $From, $secStringPassword
$myargs = @{
From = $From
To = $To
Subject = "$(Get-Date -Format (Get-Culture).DateTimeFormat.SortableDateTimePattern) test from $($From) to $($To)"
Body = "Hello Please blinking heck I hope you get this Richard"
SmtpServer = "smtp.office365.com"
Credential = $msolcred
Port = "587"
UseSsl = $true
}
[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
Send-MailMessage @myargs
But it threw an error every time:
Send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail.
[ME2PR01CA0139.ausprd01.prod.outlook.com]
Send-MailMessage works with the user password but not an App Password
Interestingly if I used the Office 365 Users actual password it would work! So my diagnosis is that Send-MailMessage is trying to network style windows credential auth and not doing the SMTP “AUTH LOGIN”
So plan B was try an open source alternative
Use PHPMailer to Test SMTP Auth Against Office 365
So PHPMailer to the rescue. I think this works because it doesn’t try to do a Microsoft login but uses AUTH LOGIN
<?php
//Import PHPMailer classes into the global namespace
//These must be at the top of your script, not inside a function
use PHPMailer\PHPMailer\PHPMailer;
use PHPMailer\PHPMailer\SMTP;
use PHPMailer\PHPMailer\Exception;
//Load Composer's autoloader
require 'vendor/autoload.php';
$relayAccount = "[email protected]";
$from = '[email protected]';
$appPassword = 'my_app_password_here';
$to = '[email protected]';
//Create an instance; passing `true` enables exceptions
$mail = new PHPMailer(true);
try {
//Server settings
$mail->SMTPDebug = SMTP::DEBUG_SERVER; //Enable verbose debug output
$mail->isSMTP(); //Send using SMTP
$mail->Host = 'smtp.office365.com'; //Set the SMTP server to send through
$mail->SMTPAuth = true; //Enable SMTP authentication
$mail->Username = $relayAccount; //SMTP username
$mail->Password = $appPassword; //SMTP password
//$mail->SMTPSecure = PHPMailer::ENCRYPTION_SMTPS; //Enable implicit TLS encryption
$mail->SMTPSecure = PHPMailer::ENCRYPTION_STARTTLS; //Enable implicit TLS encryption
$mail->Port = 587; //TCP port to connect to; use 587 if you have set `SMTPSecure = PHPMailer::ENCRYPTION_STARTTLS`
//Recipients
$mail->setFrom($from, 'Joe User');
$mail->addAddress($to); //Name is optional
//Content
$mail->isHTML(true); //Set email format to HTML
$mail->Subject = 'Here is the subject regarding N-Central Relay';
$mail->Body = 'This is the HTML message body <b>in bold!</b>';
$mail->AltBody = 'This is the body in plain text for non-HTML mail clients';
$mail->send();
echo 'Message has been sent';
} catch (Exception $e) {
echo "Message could not be sent. Mailer Error: {$mail->ErrorInfo}";
}
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