Gmail Authentication failed

[Ian Welerson]

Hello,
I'm having a problem with the authentication of my emails when I try to use in web mail clients like Gmail or Outlook.
I release port 587 in Plesk but when I try to authenticate displays the error below.
I've done all user checks and password and everything is correct.
I exchange the Postfix mail client for Qmail and the problem does not happen more, but when I go back to Postfix the problem returns.
The connection via POP is normal only via SMTP.
I can use the webmail roundcube usually the problem occurs only in SMTP authentication on external email client servers.
I configure using port 587 and TLS connection.
Could anyone help me?

Error message in Gmail:

Authentication failed. Check your username / password.
[Server response: 334 PDQxMzk0NTU3MTIuMTk4OTU1QHZwczc0NTE2LnZwcy5vdmguY2E + 535 5.7.8 Error: authentication failed: authentication failure code (535)]

 

[Dave W]

Check your configuration using a mail client like Thunderbird?

 

[Ian Welerson]

Yes, when i try use the Thunderbird the error message is:

Sending of the message failed.
The message could not be sent using Outgoing server (SMTP) smtp.naopera.com.br for an unknown reason. Please verify that your Outgoing server (SMTP) settings are correct and try again.

 

[Lloyd_mcse]

Hi Ian Welerson,
could you please post some further information to help in the investigation...

- What version of Plesk you are using
- Are you using Postfix or Qmail
- What OS
- Logs

Here's a list of log locations...

https://kb.plesk.com/en/111283

Once we can see what errors are thrown in the /var/log/mail.log it will/should help
Thanks
Regards

 

[Ian Welerson]

Hi Ian Welerson,
could you please post some further information to help in the investigation...

- What version of Plesk you are using
- Are you using Postfix or Qmail
- What OS
- Logs

Here's a list of log locations...

https://kb.plesk.com/en/111283

Once we can see what errors are thrown in the /var/log/mail.log it will/should help
Thanks
Regards

Thanks for your attention, here's the information:

- What version of Plesk you are using: Plesk v12.5.30_build1205150826.19
- Are you using Postfix or Qmail: Postfix. The error is only in Postfix, in Qmail the connection working okay.
- What OS: CentOS 6.7 (Final)‬
- Logs (/usr/local/psa/var/log/maillog):

Apr 5 03:54:51 vps74516 postfix/smtpd[18716]: connect from researchscan257.eecs.umich.edu[141.212.122.2]
Apr 5 03:54:51 vps74516 postfix/smtpd[18716]: lost connection after CONNECT from researchscan257.eecs.umich.edu[141.212.122.2]
Apr 5 03:54:51 vps74516 postfix/smtpd[18716]: disconnect from researchscan257.eecs.umich.edu[141.212.122.2]
Apr 5 03:58:11 vps74516 postfix/anvil[18718]: statistics: max connection rate 1/60s for (smtps:141.212.122.2) at Apr 5 03:54:51
Apr 5 03:58:11 vps74516 postfix/anvil[18718]: statistics: max connection count 1 for (smtps:141.212.122.2) at Apr 5 03:54:51
Apr 5 03:58:11 vps74516 postfix/anvil[18718]: statistics: max cache size 1 at Apr 5 03:54:51
Apr 5 04:16:28 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.8]
Apr 5 04:16:28 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.8], port=[33579]
Apr 5 04:16:28 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.8], port=[33579], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 04:21:11 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.10]
Apr 5 04:21:11 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.10], port=[36398]
Apr 5 04:21:11 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.10], port=[36398], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 04:30:23 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.38]
Apr 5 04:30:23 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.38], port=[33004]
Apr 5 04:30:23 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.38], port=[33004], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 04:34:05 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.28]
Apr 5 04:34:05 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.28], port=[36688]
Apr 5 04:34:06 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.28], port=[36688], top=0, retr=0, rcvd=24, sent=96, time=1
Apr 5 05:16:29 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.161.166]
Apr 5 05:16:29 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.161.166], port=[33335]
Apr 5 05:16:29 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.161.166], port=[33335], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 05:24:18 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.27]
Apr 5 05:24:18 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.27], port=[35053]
Apr 5 05:24:19 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.27], port=[35053], top=0, retr=0, rcvd=24, sent=96, time=1
Apr 5 05:35:29 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.40]
Apr 5 05:35:29 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.40], port=[33283]
Apr 5 05:35:30 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.40], port=[33283], top=0, retr=0, rcvd=24, sent=96, time=1
Apr 5 05:42:05 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.40]
Apr 5 05:42:05 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.40], port=[34101]
Apr 5 05:42:05 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.40], port=[34101], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 06:22:38 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.5]
Apr 5 06:22:38 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.5], port=[32926]
Apr 5 06:22:38 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.5], port=[32926], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 06:38:29 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.161.139]
Apr 5 06:38:29 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.161.139], port=[35273]
Apr 5 06:38:29 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.161.139], port=[35273], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 06:38:39 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.18]
Apr 5 06:38:39 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.18], port=[34065]
Apr 5 06:38:39 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.18], port=[34065], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 06:46:58 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.161.152]
Apr 5 06:46:58 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.161.152], port=[33859]
Apr 5 06:46:58 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.161.152], port=[33859], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 07:33:54 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.21]
Apr 5 07:33:55 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.21], port=[36697]
Apr 5 07:33:55 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.21], port=[36697], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 07:41:37 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.11]
Apr 5 07:41:37 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.11], port=[33094]
Apr 5 07:41:37 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.11], port=[33094], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 07:50:27 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.30]
Apr 5 07:50:27 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.30], port=[34142]
Apr 5 07:50:27 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.30], port=[34142], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 07:57:52 vps74516 courier-pop3d: Connection, ip=[::ffff:209.85.213.23]
Apr 5 07:57:52 vps74516 courier-pop3d: LOGIN, [email protected], ip=[::ffff:209.85.213.23], port=[34519]
Apr 5 07:57:52 vps74516 courier-pop3d: LOGOUT, [email protected], ip=[::ffff:209.85.213.23], port=[34519], top=0, retr=0, rcvd=24, sent=96, time=0
Apr 5 07:58:35 vps74516 postfix/smtpd[19958]: connect from unknown[59.11.218.248]
Apr 5 07:58:37 vps74516 postfix/smtpd[19958]: NOQUEUE: reject: RCPT from unknown[59.11.218.248]: 454 4.7.1 <[email protected]>: Relay access denied; from=<[email protected]> to=<[email protected]> proto=ESMTP helo=<mail.yahoo.com>
Apr 5 07:58:37 vps74516 postfix/smtpd[19958]: lost connection after RCPT from unknown[59.11.218.248]
Apr 5 07:58:37 vps74516 postfix/smtpd[19958]: disconnect from unknown[59.11.218.248]
Apr 5 07:58:37 vps74516 /usr/lib64/plesk-9.0/psa-pc-remote[13209]: Message aborted.
Apr 5 07:58:37 vps74516 /usr/lib64/plesk-9.0/psa-pc-remote[13209]: Message aborted.
Apr 5 08:01:57 vps74516 postfix/anvil[19960]: statistics: max connection rate 1/60s for (smtp:59.11.218.248) at Apr 5 07:58:35
Apr 5 08:01:57 vps74516 postfix/anvil[19960]: statistics: max connection count 1 for (smtp:59.11.218.248) at Apr 5 07:58:35
"/usr/local/psa/var/log/maillog" 621L, 73224C

I'm not sure if this is the correct log, but that was in the https://kb.plesk.com/en/111283. The POP connection is working properly, but the SMTP connection presenting problem. I can not find the problems in the log, much less information from smtp login attempts that I made today.

 

[Cedric Halenria]

Hello,

I join this thread as I have exactly the same issue

Plesk 12.5.30 (update number 30 - 2nd May 2016 @ 06:34)
OS: Ubuntu Trusty all updates ok
Postfix as MTA

No problem from webmail, no problem from Thunderbird (Pop3 on port 995, smtp on port 465) but when adding to the GMail interface, same error)

A real issue for me

 

[Dave W]

For outgoing mail try using smtp on port 587 using TLS.