Apple mail fails with Submission
Ruud Voorjans
ruud.voorjans at gmail.com
Tue Dec 18 18:01:16 EET 2018
doveconf -n output:
# 2.3.2.1 (0719df592): /etc/dovecot/dovecot.conf
# Pigeonhole version 0.5.2 ()
# OS: Linux 4.18.0-12-generic x86_64 Ubuntu 18.10
# Hostname: mail.example.org
auth_debug = yes
auth_debug_passwords = yes
auth_mechanisms = plain login
auth_verbose = yes
director_mail_servers = XX.XX.XX.XX
hostname = mail.example.org
log_path = /var/log/dovecot.log
login_trusted_networks = XX.XX.XX.XX
mail_debug = yes
mail_location = mbox:~/mail:INBOX=/var/mail/%u
mail_privileged_group = mail
namespace inbox {
inbox = yes
location =
mailbox Drafts {
special_use = \Drafts
}
mailbox Junk {
special_use = \Junk
}
mailbox Sent {
special_use = \Sent
}
mailbox "Sent Messages" {
special_use = \Sent
}
mailbox Trash {
special_use = \Trash
}
prefix =
}
passdb {
args = proxy=y host=XX.XX.XX nopassword=y
driver = static
}
protocols = imap submission
service director {
fifo_listener login/proxy-notify {
mode = 0600
user = $default_login_user
}
inet_listener {
port = 9090
}
unix_listener director-userdb {
mode = 0600
}
unix_listener login/director {
mode = 0666
}
}
service imap-login {
executable = imap-login director
}
service submission-login {
executable = submission-login
}
ssl = required
ssl_cert = </etc/letsencrypt/live/mail.example.org/fullchain.pem
ssl_cipher_list =
AES256+EECDH:AES256+EDH:ECDH+AESGCM:DH+AESGCM:ECDH+AES256:DH+AES256:ECDH+AES128:DH+AES:ECDH+3DES:DH+3DES:RSA+AESGCM:RSA+AES:RSA+3DES:!aNULL:!MD5
ssl_dh = # hidden, use -P to show it
ssl_key = # hidden, use -P to show it
ssl_min_protocol = TLSv1.2
ssl_prefer_server_ciphers = yes
submission_relay_host = XX.XX.XX.XX
submission_relay_rawlog_dir = /var/log/dovecot.log
submission_relay_trusted = yes
verbose_ssl = yes
Logging:
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection created
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Received
new command: EHLO [10.225.11.41]
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Submitted
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Ready to reply
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Completed
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection state reset
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Sent: 250-mail.example.org 8BITMIME BURL imap CHUNKING
ENHANCEDSTATUSCODES SIZE STARTTLS PIPELINING
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Received
new command: STARTTLS
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS: Next to reply
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS; 220 reply: Submitted
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS: Ready to reply
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS; 220 reply: Sent: 220 2.0.0 Begin TLS negotiation now.
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Starting
TLS
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection clear
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection state reset
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
STARTTLS; 220 reply: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x10, ret=1: before SSL
initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1: before
SSL initialization
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS read client hello
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write server hello
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write certificate
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write server done
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=-1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS read client key exchange
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS read change cipher spec
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS read finished
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write change cipher spec
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2001, ret=1:
SSLv3/TLS write finished
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x20, ret=1: SSL
negotiation finished successfully
Dec 18 16:36:39 submission-login: Debug: SSL: where=0x2002, ret=1: SSL
negotiation finished successfully
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Received
new command: EHLO [XX.XX.XX.XX]
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Submitted
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Ready to reply
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Completed
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection state reset
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Sent: 250-mail.example.org 8BITMIME AUTH PLAIN LOGIN BURL
imap CHUNKING ENHANCEDSTATUSCODES SIZE PIPELINING
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
EHLO; 250 reply: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: No more
commands pending
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Received
new command: AUTH PLAIN
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH: Next to reply
Dec 18 16:36:39 auth: Debug: client in: AUTH 1 PLAIN
service=submission secured=tls session= lip=XX.XX.XX.XX
rip=XX.XX.XX.XX lport=587 rport=49679 local_name=
mail.example.org ssl_cipher=ECDHE-RSA-AES256-GCM-SHA384
ssl_cipher_bits=256 ssl_pfs= ssl_protocol=TLSv1.2 resp= (previous
base64 data may contain sensitive data)
Dec 18 16:36:39 auth: Debug: static(): lookup
Dec 18 16:36:39 auth: Debug: static(): Allowing any password
Dec 18 16:36:39 auth: Debug: client passdb out: OK 1 user=
proxy host= XX.XX.XX.XX pass=
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH; 235 reply: Submitted
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH: Ready to reply
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Trigger
output
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: Sending
replies
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH: Completed
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH; 235 reply: Sent: 235 2.7.0 Authentication successful
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH: Destroy
Dec 18 16:36:39 submission-login: Info: proxy( ): started proxying to
XX.XX.XX.XX:587: user=< >, method=PLAIN, rip=XX.XX.XX.XX,
lip=XX.XX.XX.XX, TLS, session=<>
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Disconnected: Connection closed
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]: command
AUTH; 235 reply: Destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection destroy
Dec 18 16:36:39 submission-login: Debug: smtp-server: conn [0]:
Connection state reset
Dec 18 16:36:40 submission-login: Info: proxy( ): disconnecting
XX.XX.XX.XX (Disconnected by server(0s idle, in=533, out=295)): user=< >,
method=PLAIN, rip=XX.XX.XX.XX, lip=XX.XX.XX.XX, TLS, session=<>
Dec 18 16:36:40 submission-login: Debug: SSL alert: close notify
Op di 18 dec. 2018 om 07:18 schreef Aki Tuomi <aki.tuomi at open-xchange.com>:
>
> On 18 December 2018 at 02:30 Adi Pircalabu via dovecot <
> dovecot at dovecot.org> wrote:
>
>
> On 2018-12-18 07:33, Ruud Voorjans wrote:
>
> Dear all,
>
> I'm running dovecot # 2.3.2.1 - Pigeonhole version 0.5.2 () - OS:
> Linux 4.18.0-12-generic x86_64 Ubuntu 18.10 with Submission.
> It works great except with apple mail (Iphone).
>
> I get an error with the MTA (postfix):
> ""postfix/submission/smtpd[32552]: warning: non-SMTP command from
> mail.example.org [1][xx.xx.xx.xx]: Content-Transfer-Encoding: 7bit""
>
> with other mail-client(s) (Outlook (Desktop and Iphone app)) i have no
> problem and it proxy-sends the e-mail beautiful out to the recipient.
>
> Hardly anything to do with Dovecot. When it comes to email clients Apple
> Mail has been and is still one of the worst flops (no offence intended,
> just my opinion based on personal experience). If you can reliably
> reproduce it, try and log the raw SMTP conversation between Postfix and
> the client by enabling per IP debugging in Postfix:
> postconf -e "debug_peer_level = 20"
> postconf -e "debug_peer_list = xx.xx.xx.xx"
> postfix reload
> where xx.xx.xx.xx is the unlucky client IP address.
>
> Possibly some crappy SMTP PIPELINING implementation at the Apple end,
> who knows.
>
> --
> Adi Pircalabu
>
>
> It's not unconceivable that there are bugs in submission either. Can you
> provide doveconf -n and submission rawlogs? See
> https://wiki.dovecot.org/Submission for settings.
>
> ---
> Aki Tuomi
>
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