I don't recall from which older RoundCube to which version of roundcube came later, but I encountered a problem similar to this. For me, it turned out that a variable which could be set in config.inc.php could be set and a default assignment had changed. I had to explicitly set it.

If you have a service for outbound SMTP only available internally for your RoundCube users, and it does not require smtp auth, check these settings in you config.inc.php:
$config['smtp_user'] =
$config['smtp_pass'] =

If each user does actually auth, and they use the same creds as when they login to the web interface, then the default is probably:
$config['smtp_user'] = '%u';
$config['smtp_pass'] = '%p';

If your internal smtp service does not support or allow smtp-auth, then maybe:
$config['smtp_user'] = '';
$config['smtp_pass'] = '';

Enabling auth for smtp is a good idea though as it allows your to have an audit trail for user mail, and avoids issues where one user might try to pretend to be another. When smtp-auth is used, and logged, you can get hints in logs where users may be abusing service.

If your smtp service for outgoing mail is internal only, and you never configured it to support smtp-auth, then your smtp server logs will probably tell you so.

If the smtp-auth error is generated by the smtp service and not implied by the RC application, then also consider reviewing:
$config['smtp_port'] =

Some people setup an outbound smtp service to use a port other than TCP/25 which allows for smtp-auth and possibly encryption, while the service they configured for port TCP/25 does not. You would know which service uses which. If you use encryption, test use of encryption to your smtp service port to make sure your certs are not expired, and support modern hashing/checks.

Compare/diff all of the new variables in the latest config.inc.php.sample installed with your present config.inc.php and see if any new variables are expected.

If logs and FAQ do not help, you can always try to simulate an smtp session using telnet, or with crypto using "openssl" from the command line, and complete a user auth manually. Use your favorite search engine to see examples for how-to do either, if you don't know how.

HTH

On 2020-10-19 10:14, Denny Jones wrote:
Hello,

After updating to 1.4.9 version from 1.3 I get an error when trying to
send mail.

Here's the error I'm getting:

SMTP Error (250): Authentication failed.

Where do I start sleuthing on this?

Thank,
Denny
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