This might be a really simple issue, but my searches haven’t come up with a solution yet. (only one thread where a guy said he solved it but never elaborated.)

Roundcube gives an error of "SMTP Error (250): Authentication failed.” and the log has "Must issue a STARTTLS command first."

PHP 5.6.4 Postfix 2.11.3 Roundcube 1.3.3

Things used to work just fine but it’s been a while since I’ve used roundcube to send any emails, so i haven’t noticed until now.. No self-signed certificate. Thunderbird/Apple Mail work ok.

config.inc.php has:

$config['default_host'] = 'tls://%n’; #I’ve tried ‘tls://pile.pbp.net' as well

$config['smtp_port'] = 587;

$config['smtp_user'] = '%u';

$config['smtp_pass'] = '%p’;

smtp_debug shows:

[31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 220 pile.pbp.net ESMTP Postfix (Ubuntu) [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Send: EHLO pile.pbp.net [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-pile.pbp.net [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-PIPELINING [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-SIZE 30480000 [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-ETRN [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-STARTTLS [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-ENHANCEDSTATUSCODES [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250-8BITMIME [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 250 DSN [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Send: RSET [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 530 5.7.0 Must issue a STARTTLS command first [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Send: QUIT [31-Dec-2017 14:13:15 -0600]: <jlfk3bmj> Recv: 221 2.0.0 Bye

Anything else that I should check? it is a slightly older ubuntu release (15.04) at this point. I’m looking at moving webmail to another machine with a newer install.

Thank you! — jonathan