Apple Mail asks for password on SMTP after 1.4.3 upgrade

**theemstra** · Apr 24th 2017

Logging in on Apple Mail with normal password auth over TLS (587), it asks for a password when sending an email. IMAP works fine, SMTP asks for password.

Important note (also for other mac users)

Quote from UptimeJeff

Yosemite & ElCapitan Mail.app have the new "Automatically detect and maint account settings" option. This will cause Mail.app to attempt Digest-MD5, and thats when you might see dovecot crashing.

So we cannot use this feature, I manually set port to 587, selected TLS and normal password auth (because of this).

Server info
1.4.3 on Debian Jessie, Postfix/Dovecot.
Error when password is requested: "Apr 24 10:11:04 jessie postfix/smtpd[25151]: warning: revdns[ip]: SASL LOGIN authentication failed: code"

This may or may not be related to the known issue about the unknown namespace trash, which is resolved already.

**Nuxwin** · Apr 24th 2017

@theemstra

There is no bug. I'm using Icedove (Thunderbird) under Debian which also provides discovering feature for mail account parameters. In my case all went good. Discovered parameters are those expected: For instance with the nuxwin@bbox.nuxwin.com account, I get:

discovering_mail_01.png discovering_mail_02.png

There is only the identifier to adjust which must be the full email address and also the IMAP and SMTP server names in case the names don't matche with your server hostname and only if those names are not also added in the SSL certificate (subject alternative names)...

When using discovering feature, many login attempt are made on both SMTP and IMAP servers, resulting to many failure logs. For instance, logs from my discovering session are:

Shell-Script

root@www:~# clear && tail -fn0 /var/log/mail.log
Apr 24 15:51:17 www postfix/smtpd[15879]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www dovecot: imap-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=</Ya55ulNrwDAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<zYe55ulNugDAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<LIq55ulNuQDAqAEB>
Apr 24 15:51:17 www dovecot: imap-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<bI655ulNsADAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<vpC55ulNuwDAqAEB>
Apr 24 15:51:17 www postfix/smtpd[15879]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:17 www postfix/smtpd[15879]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15884]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:17 www postfix/smtpd[15879]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:17 www dovecot: imap-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<Jqm55ulNsQDAqAEB>
Apr 24 15:51:17 www postfix/smtpd[15880]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www dovecot: imap-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<aLq55ulNtgDAqAEB>
Apr 24 15:51:17 www postfix/smtpd[15880]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15884]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:17 www postfix/smtpd[15880]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15886]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15884]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www dovecot: pop3-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<Ucq55ulNvADAqAEB>
Apr 24 15:51:17 www postfix/smtpd[15884]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:17 www postfix/smtpd[15880]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: connect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15879]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www dovecot: imap-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<6N655ulNtwDAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<GuC55ulNwADAqAEB>
Apr 24 15:51:17 www postfix/smtpd[15886]: lost connection after CONNECT from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15886]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: lost connection after CONNECT from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15880]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15884]: lost connection after CONNECT from unknown[192.168.1.1]
Apr 24 15:51:17 www postfix/smtpd[15884]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:17 www dovecot: pop3-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<Qfa55ulNwQDAqAEB>
Apr 24 15:51:17 www dovecot: imap-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<O/u55ulNuADAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<mgu65ulNwgDAqAEB>
Apr 24 15:51:17 www dovecot: pop3-login: Disconnected (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<CiG65ulNwwDAqAEB>
Apr 24 15:51:38 www postfix/smtpd[15893]: connect from unknown[192.168.1.1]
Apr 24 15:51:38 www postfix/smtpd[15893]: improper command pipelining after EHLO from unknown[192.168.1.1]: QUIT\r\n
Apr 24 15:51:38 www postfix/smtpd[15893]: disconnect from unknown[192.168.1.1]
Apr 24 15:51:38 www dovecot: imap-login: Aborted login (no auth attempts in 0 secs): user=<>, rip=192.168.1.1, lip=192.168.1.133, session=<dSz85+lNygDAqAEB>
Apr 24 15:51:46 www dovecot: imap-login: Login: user=<nuxwin@bbox.nuxwin.com>, method=PLAIN, rip=192.168.1.1, lip=192.168.1.133, mpid=15906, TLS, session=<Qh906OlNzADAqAEB>
Apr 24 15:51:46 www dovecot: imap(nuxwin@bbox.nuxwin.com): Disconnected: Logged out in=8 out=401

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These are expected.

Note that if your client was previously configured to use non-plaintext auth, that is normal that you get asked again for password.
Here there is no bug on our side.

**theemstra** · Apr 24th 2017

Hi @Nuxwin,

Thanks for checking out this situation.
I visited the client just now and configured the account in Outlook for Mac, this way it worked just fine.
Just Apple Mail seems to be complaining. Maybe Apple Mail doesn't support the plaintext or normal password tls/ssl login?

**Nuxwin** · Apr 24th 2017

Quote from theemstra

Just Apple Mail seems to be complaining. Maybe Apple Mail doesn't support the plaintext or normal password tls/ssl login?

That would be really curious and this would make their application not compatible with several mail services... They should have a support forum or something like this. Just ask them. Normally, a mail client shouldn't try to use an authentication method that is not provided by the server (IMAP or SMTP, whatever). IMAP and SMTP servers clearly announce the supported authentication mechanisms. For instance:

IMAP server (here Dovecot)

Shell-Script

root@dev:~# telnet localhost 143Trying 127.0.0.1...Connected to dev.nuxwin.com.local.Escape character is '^]'.* OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE IDLE STARTTLS AUTH=PLAIN AUTH=LOGIN] Dovecot ready.

Here you can see that supported authentication mechanisms are PLAIN and LOGIN (both are same, that is: plain password). LOGIN is there to ensure compatibility with older mail clients (microsoft).

SMTP (here postfix)

Shell-Script

root@dev:~# telnet localhost 587
Trying 127.0.0.1...
Connected to dev.nuxwin.com.local.
Escape character is '^]'.
220 dev.nuxwin.com ESMTP i-MSCP 1.4.3 Managed
EHLO localhost
250-dev.nuxwin.com
250-PIPELINING
250-SIZE
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250 SMTPUTF8
quit
221 2.0.0 Bye
Connection closed by foreign host.

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Same thing here, supported authentication mechanisms are clearly announced

**FloRet88** · Apr 24th 2017

Hello @theemstra

Should be supported!! Apple has a few entrys in their KB regarding their authentification!

Best regards

**theemstra** · Apr 24th 2017

Interesting. I'll report back if I find anything.

**Nuxwin** · Apr 24th 2017

@theemstra

I've edited my previous answer.

**Nuxwin** · Apr 25th 2017

Quote from FloRet88

Should be supported!! Apple has a few entrys in their KB regarding their authentification!

Could you provide us with a link to those KB?

@theemstra

Apple mail is an iphone APP? If yes, I could give a try with my really old iphone (first serie)...

**theemstra** · Apr 25th 2017

Nope, it's on Mac OS X Apple Mail, the latest version.

**FloRet88** · Apr 25th 2017

Hello,

I haveńt found the KB, that i found yesterday - have to look tomorrow on my workstation!!

But here says one of their KB´s that all is supported: https://support.apple.com/kb/PH22345?locale=en_US

Best regards.

Apple Mail asks for password on SMTP after 1.4.3 upgrade

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