SMTP not working with GMail

[Former user]

Hi guys,

I've been trying to attach my mail server through Gmail account, where you can you own email to be used through external SMTP server.

This is the error message which Google returns:

Authentication failed. Please check your username/password.
[Server response: Missed upload deadline (9.99s) (state SENT_EHLO) code(0) ]

I'm double sure that the username ( in the format of [e-mail] ) and the password are the correct ones ( works straightforward with POP3 part ).

I tested with all the combinations of ports and secure options ( 25 -> TLS,SSL,no one, 465 -> SSL,TLS, 587 -> SSL,TLS ) and the actual one which returns that message is 465:SSL.

Any help would be really appreciated! Kind regards :)

[Former user]

Hey guys,

any news on this?

Thanks in advance!

[SH]

Hi,

could you please add steps for reproduce? I cant find anything about external SMTP in my gmail...

Thanks

[Former user]

Hi,

please see https://support.google.com/mail/answer/22370?hl=en section "I'm a Gmail or Google Apps user sending from an external address."

Thanks again, Julian

[SH]

Ha, thanks, i got it working at first try.

used whole email address and port 587...

[SH]

please try latest mailserver image

[Former user]

Ok just pulled the latest version and tested right now.

The good news is that the error in the OP is no more there but...now I have a second kind of error:

Authentication failed. Please check your username/password.
[Server response: Missed upload deadline (9.49s) (state SENT_SECOND_EHLO) code(0) ]

This happens with Full Email ( and password ), TLS + 587 port.

Which is impossible, the username and passwords are actually working on the POP3 side, why it shouldn't work on SMTP? The data was preserved from the old version of the Docker FYI. Any idea?

Thanks in advance!

// EDIT: Using MXToolbox over the SMTP, I found this:

Could this be the issue with SMTP and related to the error? If so, any idea on how can I fix it?

[SH]

There is one log which can help - please look at /{your-data-folder}/log/qpsmtpd/2016-04-29/ - every file there should mean one smtp connection, there should be gmail connection log with some additional info

[Former user]

This is what I get

2016-04-28 21:02:41 [3XkATDMd] 209.85.215.44:36195 ()  ->  - [] 550 Connecting host started transmitting before SMTP greeting
2016-04-28 21:03:28 [eZJH6skQ] 155.133.82.70:53958 ()  ->  - [] 500 Unrecognized command
2016-04-28 21:07:12 [unj0GFdM] 209.85.215.54:35785 ()  ->  - [] 550 Cannot establish SSL session

and this is the log

2016-04-28 21:02:22 [fcrdns] - karma 1 (1)
2016-04-28 21:02:22 [fcrdns] - pass
2016-04-28 21:02:23 [earlytalker] - pass, not spontaneous
2016-04-28 21:02:23 [relay] - skip, no match
2016-04-28 21:02:24 [dnsbl] - pass
2016-04-28 21:02:24 - 220 mail.julianxhokaxhiu.com ESMTP
2016-04-28 21:02:24 - dispatching EHLO mail-lf0-f52.google.com
2016-04-28 21:02:24 [helo] - karma -1 (0)
2016-04-28 21:02:24 [helo] - fail, tolerated, invalid localhost
2016-04-28 21:02:24 - 250-mail.julianxhokaxhiu.com Hi mail-lf0-f52.google.com [209.85.215.52]
2016-04-28 21:02:24 - 250-PIPELINING
2016-04-28 21:02:24 - 250-8BITMIME
2016-04-28 21:02:24 - 250 STARTTLS
2016-04-28 21:02:24 - dispatching STARTTLS
2016-04-28 21:02:24 - 220 Go ahead with TLS
2016-04-28 21:02:24 [tls] - TLS setup returning
2016-04-28 21:02:24 - dispatching EHLO mail-lf0-f52.google.com
2016-04-28 21:02:24 [helo] - karma -1 (-1)
2016-04-28 21:02:24 [helo] - fail, tolerated, invalid localhost
2016-04-28 21:02:24 - 250-mail.julianxhokaxhiu.com Hi mail-lf0-f52.google.com [209.85.215.52]
2016-04-28 21:02:24 - 250-PIPELINING
2016-04-28 21:02:24 - 250-8BITMIME
2016-04-28 21:02:24 - 250 AUTH PLAIN LOGIN
2016-04-28 21:02:24 - dispatching AUTH PLAIN ***

[Former user]

Any clue on this?

[SH]

This line is the problem: "550 Connecting host started transmitting before SMTP greeting"

Its one of SPAM filtering method - wait a second and then send greeting. If client ignores RFC it sends hello message before greeting. It was working for me, if you have some way to contact google support then you should tell them. Otherwise it can be switched off internally with removing line "earlytalker" in /etc/qpsmtpd/plugins ...

[SH]

Closing...

[Former user]

Sorry but I don't know why, I got to see this topic only today, and via email notification.

May I ask you if it's possible to change the plugin configuration outside of the docker itself, using a volume maybe? I don't want to play with dockers inside, I prefer to configure them from the outside. Contacting Google about these issues, is like shooting in the dark. Most probably you'll not hit anyone...so if I can do it myself it's better.

Thank you in advance!

---

I was considering that maybe the plugins may be a setting in the .ini file! That would be awesome :)

[Former user]

@analogic I found where is living the issue, and it's totally unrlated to qpsmtpd!

I enabled the logs of dovecot by editing /etc/dovecot/conf.d/10-logging.conf and setting log_path = /var/log/dovecot.log ( highly suggested to keep this into the log folder, otherwise it just gets lost ), I finally got this log, which finally make sense, why on qpsmtpd side the log stops after dispatching AUTH PLAN!

Oct 20 18:53:21 master: Info: Dovecot v2.2.22 (fe789d2) starting up for imap, sieve, pop3
Oct 20 18:54:10 auth: Error: BUG: Authentication client sent unknown command: ZQ==
Oct 20 18:54:10 auth: Panic: key not found from hash
Oct 20 18:54:10 auth: Error: Raw backtrace: /usr/lib/dovecot/libdovecot.so.0(+0x7aee2) [0x7f54f32f8ee2] -> /usr/lib/dovecot/libdovecot.so.0(+0x7afcd) [0x7f54f32f8fcd] -> /usr/lib/dovecot/libdovecot.so.0(i_fatal+0) [0x7f54f329da61] -> dovecot/auth(+0x1809c) [0x55d815d2809c] -> dovecot/auth(+0x1828d) [0x55d815d2828d] -> dovecot/auth(auth_request_handler_reply+0x139) [0x55d815d28ce9] -> dovecot/auth(+0x16f35) [0x55d815d26f35] -> dovecot/auth(auth_request_verify_plain_callback+0x48) [0x55d815d26fb8] -> dovecot/auth(+0x28291) [0x55d815d38291] -> dovecot/auth(+0x1dbca) [0x55d815d2dbca] -> /usr/lib/dovecot/libdovecot.so.0(io_loop_call_io+0x4c) [0x7f54f330cc6c] -> /usr/lib/dovecot/libdovecot.so.0(io_loop_handler_run_internal+0x101) [0x7f54f330e101] -> /usr/lib/dovecot/libdovecot.so.0(io_loop_handler_run+0x25) [0x7f54f330ccf5] -> /usr/lib/dovecot/libdovecot.so.0(io_loop_run+0x38) [0x7f54f330ce98] -> /usr/lib/dovecot/libdovecot.so.0(master_service_run+0x13) [0x7f54f32a3583] -> dovecot/auth(main+0x38f) [0x55d815d1e90f] -> /lib/x86_64-linux-gnu/libc.so.6(__libc_start_main+0xf0) [0x7f54f288b830] -> dovecot/auth(_start+0x29) [0x55d815d1eb19]
Oct 20 18:54:10 auth: Fatal: master: service(auth): child 617 killed with signal 6 (core dumped)

Any idea? I suspect the plugin auth/auth-dovecot ( https://poste.io/qpsmtpd/auth-dovecot ) on qpsmtpd side is broken somehow. Can you please take a look at it?

[Former user]

Bump?

[MA]

I got the same issue. I can´t even use SMTP at all. Removing the earlytalkerplugin didn`t work either. Seems to be a breaking dovecot bug in the auth plugin

[Sophie L]

Still seeing this with google. 550 Connecting host started transmitting before SMTP greeting when sending email from gmail web browser ( chrome) and sending to poste.io

[Sophie L]

I'm seeing this with all servers running postix + tls sending email to poste.io: "Connecting host started transmitting before SMTP greeting"

[Dome]

Got probably the same issue. No fix so far? Thanks for nothing poste.io.... If they cant even fix their free stuff - how is their paid stuff going to work? Searching for a new mailserver replacement like this now wich maybe WORKS and doesnt require 1000 config steps, I'll donate you a beer for a useful tip. KThxBye

[SH]

Can you please try again with 2.0 image?

There is whole new and different delivery service - and there will be also detailed transaction logs at log/delivery

[SH]

Tested, working ok now. Closing