Microsoft 365 SMTP Issue

[maxmueller89]

Hi guys,

I have set up 4 mailboxes in my Freescout installation. 3 of them work perfectly with sending and fetching emails including sending the test email. Unfortuantely the fourth box is a Microsoft 365 email address. It does fetch but sending including sending test email is not working.

I get this error:

Fehler senden. Failed to authenticate on SMTP server with username "office@fairschenkt.at" using 2 possible authenticators. Authenticator LOGIN returned Swift_TransportException: Expected response code 235 but got code "535", with message "535 5.7.3 Authentication unsuccessful [AM0PR07CA0005.eurprd07.prod.outlook.com] " in /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/AbstractSmtpTransport.php:457 Stack trace: #0 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/AbstractSmtpTransport.php(341): Swift_Transport_AbstractSmtpTransport->assertResponseCode('535 5.7.3 Authe...', Array) #1 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/EsmtpTransport.php(305): Swift_Transport_AbstractSmtpTransport->executeCommand('U3VmMzE5OTk=\r\n', Array, Array, false, NULL) #2 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/Esmtp/Auth/LoginAuthenticator.php(36): Swift_Transport_EsmtpTransport->executeCommand('U3VmMzE5OTk=\r\n', Array) #3 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/Esmtp/AuthHandler.php(177): Swift_Transport_Esmtp_Auth_LoginAuthenticator->authenticate(Object(Swift_SmtpTransport), 'office@fairsche...', 'Suf31999') #4 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/EsmtpTransport.php(371): Swift_Transport_Esmtp_AuthHandler->afterEhlo(Object(Swift_SmtpTransport)) #5 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/AbstractSmtpTransport.php(148): Swift_Transport_EsmtpTransport->doHeloCommand() #6 /var/www/html/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Mailer.php(65): Swift_Transport_AbstractSmtpTransport->start() #7 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(451): Swift_Mailer->send(Object(Swift_Message), Array) #8 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(235): Illuminate\Mail\Mailer->sendSwiftMessage(Object(Swift_Message)) #9 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/Mailable.php(125): Illuminate\Mail\Mailer->send('emails/user/not...', Array, Object(Closure)) #10 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(250): Illuminate\Mail\Mailable->send(Object(Illuminate\Mail\Mailer)) #11 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(205): Illuminate\Mail\Mailer->sendMailable(Object(App\Mail\UserNotification)) #12 /var/www/html/vendor/laravel/framework/src/Illuminate/Mail/PendingMail.php(99): Illuminate\Mail\Mailer->send(Object(App\Mail\UserNotification)) #13 /var/www/html/app/Jobs/SendNotificationToUsers.php(121): Illuminate\Mail\PendingMail->send(Object(App\Mail\UserNotification)) #14 [internal function]: App\Jobs\SendNotificationToUsers->handle() #15 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(29): call_user_func_array(Array, Array) #16 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(87): Illuminate\Container\BoundMethod::Illuminate\Container{closure}() #17 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(31): Illuminate\Container\BoundMethod::callBoundMethod(Object(Illuminate\Foundation\Application), Array, Object(Closure)) #18 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/Container.php(549): Illuminate\Container\BoundMethod::call(Object(Illuminate\Foundation\Application), Array, Array, NULL) #19 /var/www/html/vendor/laravel/framework/src/Illuminate/Bus/Dispatcher.php(94): Illuminate\Container\Container->call(Array) #20 /var/www/html/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(114): Illuminate\Bus\Dispatcher->Illuminate\Bus{closure}(Object(App\Jobs\SendNotificationToUsers)) #21 /var/www/html/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(102): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline{closure}(Object(App\Jobs\SendNotificationToUsers)) #22 /var/www/html/vendor/laravel/framework/src/Illuminate/Bus/Dispatcher.php(98): Illuminate\Pipeline\Pipeline->then(Object(Closure)) #23 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/CallQueuedHandler.php(49): Illuminate\Bus\Dispatcher->dispatchNow(Object(App\Jobs\SendNotificationToUsers), false) #24 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Jobs/Job.php(76): Illuminate\Queue\CallQueuedHandler->call(Object(Illuminate\Queue\Jobs\DatabaseJob), Array) #25 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Worker.php(320): Illuminate\Queue\Jobs\Job->fire() #26 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Worker.php(270): Illuminate\Queue\Worker->process('database', Object(Illuminate\Queue\Jobs\DatabaseJob), Object(Illuminate\Queue\WorkerOptions)) #27 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Worker.php(114): Illuminate\Queue\Worker->runJob(Object(Illuminate\Queue\Jobs\DatabaseJob), 'database', Object(Illuminate\Queue\WorkerOptions)) #28 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Console/WorkCommand.php(101): Illuminate\Queue\Worker->daemon('database', 'emails,default,...', Object(Illuminate\Queue\WorkerOptions)) #29 /var/www/html/vendor/laravel/framework/src/Illuminate/Queue/Console/WorkCommand.php(85): Illuminate\Queue\Console\WorkCommand->runWorker('database', 'emails,default,...') #30 [internal function]: Illuminate\Queue\Console\WorkCommand->handle() #31 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(29): call_user_func_array(Array, Array) #32 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(87): Illuminate\Container\BoundMethod::Illuminate\Container{closure}() #33 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/BoundMethod.php(31): Illuminate\Container\BoundMethod::callBoundMethod(Object(Illuminate\Foundation\Application), Array, Object(Closure)) #34 /var/www/html/vendor/laravel/framework/src/Illuminate/Container/Container.php(549): Illuminate\Container\BoundMethod::call(Object(Illuminate\Foundation\Application), Array, Array, NULL) #35 /var/www/html/vendor/laravel/framework/src/Illuminate/Console/Command.php(183): Illuminate\Container\Container->call(Array) #36 /var/www/html/vendor/symfony/console/Command/Command.php(255): Illuminate\Console\Command->execute(Object(Symfony\Component\Console\Input\ArgvInput), Object(Illuminate\Console\OutputStyle)) #37 /var/www/html/vendor/laravel/framework/src/Illuminate/Console/Command.php(170): Symfony\Component\Console\Command\Command->run(Object(Symfony\Component\Console\Input\ArgvInput), Object(Illuminate\Console\OutputStyle)) #38 /var/www/html/vendor/symfony/console/Application.php(963): Illuminate\Console\Command->run(Object(Symfony\Component\Console\Input\ArgvInput), Object(Symfony\Component\Console\Output\ConsoleOutput)) #39 /var/www/html/vendor/symfony/console/Application.php(254): Symfony\Component\Console\Application->doRunCommand(Object(Illuminate\Queue\Console\WorkCommand), Object(Symfony\Component\Console\Input\ArgvInput), Object(Symfony\Component\Console\Output\ConsoleOutput)) #40 /var/www/html/vendor/symfony/console/Application.php(147): Symfony\Component\Console\Application->doRun(Object(Symfony\Component\Console\Input\ArgvInput), Object(Symfony\Component\Console\Output\ConsoleOutput)) #41 /var/www/html/vendor/laravel/framework/src/Illuminate/Console/Application.php(88): Symfony\Component\Console\Application->run(Object(Symfony\Component\Console\Input\ArgvInput), Object(Symfony\Component\Console\Output\ConsoleOutput)) #42 /var/www/html/vendor/laravel/framework/src/Illuminate/Foundation/Console/Kernel.php(121): Illuminate\Console\Application->run(Object(Symfony\Component\Console\Input\ArgvInput),

STMP: smtp.office365.com
Port: 587
Encryption: TLS

Any idea?

[freescout-helpdesk]

https://github.com/freescout-helpdesk/freescout/wiki/Connect-Microsoft-Office-365-Exchange-to-FreeScout

[maxmueller89]

Thank you for the comment.

I resolved it with using a spf entry in my DNS settings and added my internal exchange address (*.mail.protection.outlook.com) as SMTP server.