Cannot sent SMTP email after updating to EE 2.7.3 from 2.5.5

Question

So i have EE sending SMTP mail via a remote server which was all working fine in EE 2.5.5 but now i have upgraded to 2.7.3 it's not having it at all!

The error i get is:

An Error Was Encountered Unable to send email at this time.

220 brightmail.redacted.local ESMTP Symantec Messaging Gateway 

hello: 250-brightmail.redacted.local says EHLO to 111.111.111.111:41353
250-ENHANCEDSTATUSCODES
250-SIZE 15728640
250-8BITMIME
250 PIPELINING
Failed to send AUTH LOGIN command. Error: 500 5.5.2 unrecognized command 
Unable to send email using PHP SMTP. Your server might not be configured to send mail using this method.

I have got this stuff already configured:

$config['email_newline']    = "\r\n";
$config['email_crlf']       = "\r\n";

And nothing else i try has any effect.

Any help would be grand!

Answer 1

Instead of using SMTP with EE, I'd recommend using Escort (http://devot-ee.com/add-ons/escort) with a third-party 'transactional' email service like Mandrill (http://mandrill.com). We've also had issues with SMTP and PHP mail in EE (particularly Gmail deliverability), which the third-party system solved. Escort is super-easy to set up, and you get the benefits of the third-party system (better deliverability, batch sending, reporting, etc.).

Someone else may be able to specifically address your issues with SMTP, but I still think it's worth considering the third-party route.