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Topic: An error occurred!SMTP Error (535): Authentication failed.

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- iRedMail version (check /etc/iredmail-release): latest
- Linux/BSD distribution name and version:  centos 6.7
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): SQL
- Web server (Apache or Nginx): Apache
- Manage mail accounts with iRedAdmin-Pro? NO
- Related log if you're reporting an issue:
====
I getthis error when trying to send via roundcube
An error occurred!SMTP Error (535): Authentication failed.

I see this in the mailog:
Mar  7 18:04:09 parra-gw1 roundcube: <vk9doqnj> SMTP Error: Authentication failure: Invalid response code received from server (Code: 535) in /var/www/roundcubemail-1.1.4/program/lib/Roundcube/rcube.php on line 1712 (POST /mail/?_task=mail&_unlock=loading1457395447624&_lang=en_US&_framed=1?_task=mail&_action=send)

using thunderbird to send I get this authentication failed and the log show this:
Mar  7 18:07:40 parra-gw1 postfix/submission/smtpd[3233]: warning: xxxxxxxxxxs[x.x.x.x1]: SASL PLAIN authentication failed:
Mar  7 18:07:46 parra-gw1 postfix/submission/smtpd[3233]: warning: xxxxxxxxxx[x.x.x.x]: SASL LOGIN authentication failed: UGFzc3dvcmQ6

I was trying to get the system to allow plain text authentication from those machines in the private network and after I got that working I can no longer send from the public side or roundcube.

any hints is appreciated.

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Re: An error occurred!SMTP Error (535): Authentication failed.

*) It's hard to help without sharing with us what you actually changed.
*) If your internet networks/devices support sending email with STARTTLS protocol, please use STARTTLS. If not, try this tutorial:
http://www.iredmail.org/docs/additional.smtp.port.html

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Re: An error occurred!SMTP Error (535): Authentication failed.

ZhangHuangbin wrote:

*) It's hard to help without sharing with us what you actually changed.
*) If your internet networks/devices support sending email with STARTTLS protocol, please use STARTTLS. If not, try this tutorial:
http://www.iredmail.org/docs/additional.smtp.port.html

I just followed the howto
http://www.iredmail.org/docs/allow.inse … tions.html
/usr/local/etc/dovecot/dovecot.conf
disable_plaintext_auth=no
ssl=yes

I also turned off greylisting. and added
mynetworks = 127.0.0.0/8, 192.168.101.0/24
and
smtpd_helo_restrictions =
#    reject_non_fqdn_helo_hostname
#    reject_invalid_helo_hostname

Unfortunately outlook does not support STARTTLS and I have too many of them to mess with.

I do have it working where I can send and receiving using outlook and plain text.

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Re: An error occurred!SMTP Error (535): Authentication failed.

Seems that you messed up some configurations. With default iRedMail settings, Roundcube webmail and Thunderbird should work fine with STARTTLS. For internal network devices or mail client applications, this tutorial is better:
http://www.iredmail.org/docs/additional.smtp.port.html

It keeps default security settings, but still allows you to use insecure network connection for INTERNAL network devices or mail client applications.

If you have new errors, please paste the original error message here, also related log in Postfix/Dovecot log files.

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Re: An error occurred!SMTP Error (535): Authentication failed.

SOLVED
My mistake, I am moving a customer to ired so I imported the list of users from an old server, unfortunately the enablesmtp and enablesmtpsecure fields values in the mailbox table was imported inverted and set to zero.
The confusion on my side was because of message returned is misleading to say the least.
"An error occurred!SMTP Error (535): Authentication failed." sending me to look elsewhere.
It should say: "User blocked from sending, contact your system manager"