Outlook Problems with SMTP Port 587

[Stefan Becker]

Hi,

i install a new server with Debian 7.4 and Plesk Panel 11.5 with all MU.

Now i have a problem with sending mails about port 587.

This is an SMTP dialog about port 25

250-PIPELINING
250-SIZE 51200000
250-ETRN
250-STARTTLS
250-AUTH DIGEST-MD5 CRAM-MD5 PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

Her is an dialog with port 587

250-PIPELINING
250-SIZE 51200000
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

I don't see the authentication method, and so MS Outlook doesn't work fine :-(

Have somebody a solution?

Best regards,

Stefan

 

[Stefan Becker]

Now in found this KB http://kb.parallels.com/en/113866, but under Debian 7 i don't find the file '/usr/lib64/sasl2/smtpd.conf'

Have anyone an idea?

Stefan

 

[Lloyd_mcse]

On Ubuntu this file is in...

/etc/postfix/sasl2/smtpd.conf

It should be the same.

 

[Stefan Becker]

Hi Loyd,

of course i find this file at this location. But i think, this is ok

pwcheck_method: auxprop saslauthd
auxprop_plugin: plesk
saslauthd_path: /private/plesk_saslauthd
mech_list: DIGEST-MD5 CRAM-MD5 PLAIN LOGIN
auto_transition: yes
sql_engine: intentionally disabled
log_level: 4

Or not?!

 

[Lloyd_mcse]

Yeah, that's what I have.

 

[Stefan Becker]

So, i don't understand for this difference :-(

 

[Lloyd_mcse]

So just to confirm you have enabled "Submission" in...

Plesk -> Tools & Settings -> Mail Settings

What does your /etc/postfix/main.cf and /etc/postfix/master.cf look like? Has submission been enabled properly?

 

[Stefan Becker]

So just to confirm you have enabled "Submission" in...

Of course ;-)

What does your /etc/postfix/main.cf and /etc/postfix/master.cf look like? Has submission been enabled properly?

My master.cf

#
# Postfix master process configuration file.  For details on the format
# of the file, see the master(5) manual page (command: "man 5 master").
#
# Do not forget to execute "postfix reload" after editing this file.
#
# ==========================================================================
# service type  private unpriv  chroot  wakeup  maxproc command + args
#               (yes)   (yes)   (yes)   (never) (100)
# ==========================================================================
smtp      inet  n       -       -       -       -       smtpd
#smtp      inet  n       -       -       -       1       postscreen
#smtpd     pass  -       -       -       -       -       smtpd
#dnsblog   unix  -       -       -       -       0       dnsblog
#tlsproxy  unix  -       -       -       -       0       tlsproxy
#submission inet n       -       -       -       -       smtpd
#  -o syslog_name=postfix/submission
#  -o smtpd_tls_security_level=encrypt
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#smtps     inet  n       -       -       -       -       smtpd
#  -o syslog_name=postfix/smtps
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#628       inet  n       -       -       -       -       qmqpd
pickup fifo n - - 60 1 pickup
cleanup   unix  n       -       -       -       0       cleanup
qmgr fifo n - n 1 1 qmgr
#qmgr     fifo  n       -       n       300     1       oqmgr
tlsmgr    unix  -       -       -       1000?   1       tlsmgr
rewrite   unix  -       -       -       -       -       trivial-rewrite
bounce    unix  -       -       -       -       0       bounce
defer     unix  -       -       -       -       0       bounce
trace     unix  -       -       -       -       0       bounce
verify    unix  -       -       -       -       1       verify
flush     unix  n       -       -       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       -       -       -       smtp
relay     unix  -       -       -       -       -       smtp
#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
showq     unix  n       -       -       -       -       showq
error     unix  -       -       -       -       -       error
retry     unix  -       -       -       -       -       error
discard   unix  -       -       -       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       -       -       -       lmtp
anvil     unix  -       -       -       -       1       anvil
scache    unix  -       -       -       -       1       scache
#
# ====================================================================
# Interfaces to non-Postfix software. Be sure to examine the manual
# pages of the non-Postfix software to find out what options it wants.
#
# Many of the following services use the Postfix pipe(8) delivery
# agent.  See the pipe(8) man page for information about ${recipient}
# and other message envelope options.
# ====================================================================
#
#
# maildrop. See the Postfix MAILDROP_README file for details.
# Also specify in main.cf: maildrop_destination_recipient_limit=1
#
maildrop  unix  -       n       n       -       -       pipe
  flags=DRhu user=vmail argv=/usr/bin/maildrop -d ${recipient}
#
# ====================================================================
#
# Recent Cyrus versions can use the existing "lmtp" master.cf entry.
#
# Specify in cyrus.conf:
#   lmtp    cmd="lmtpd -a" listen="localhost:lmtp" proto=tcp4
#
# Specify in main.cf one or more of the following:
#  mailbox_transport = lmtp:inet:localhost
#  virtual_transport = lmtp:inet:localhost
#
# ====================================================================
#
# Cyrus 2.1.5 (Amos Gouaux)
# Also specify in main.cf: cyrus_destination_recipient_limit=1
#
#cyrus     unix  -       n       n       -       -       pipe
#  user=cyrus argv=/cyrus/bin/deliver -e -r ${sender} -m ${extension} ${user}
#
# ====================================================================
# Old example of delivery via Cyrus.
#
#old-cyrus unix  -       n       n       -       -       pipe
#  flags=R user=cyrus argv=/cyrus/bin/deliver -e -m ${extension} ${user}
#
# ====================================================================
#
# See the Postfix UUCP_README file for configuration details.
#
uucp      unix  -       n       n       -       -       pipe
  flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)
#
# Other external delivery methods.
#
ifmail    unix  -       n       n       -       -       pipe
  flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient)
bsmtp     unix  -       n       n       -       -       pipe
  flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient
scalemail-backend unix  -       n       n       -       2       pipe
  flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} ${user} ${extension}
mailman unix - n n - - pipe flags=R user=list:list argv=/usr/lib/plesk-9.0/postfix-mailman ${nexthop} ${user} ${recipient}


plesk_virtual unix - n n - - pipe flags=DORhu user=popuser:popuser argv=/usr/lib/plesk-9.0/postfix-local -f ${sender} -d ${recipient} -p /var/qmail/mailnames
plesk_saslauthd unix y y y - 1 plesk_saslauthd status=5 listen=6 dbpath=/plesk/passwd.db
smtps inet n - - - - smtpd -o smtpd_tls_wrappermode=yes


85.10.210.154-2a01-4f8-130-9301--3 unix - n n - - smtp -o smtp_bind_address=85.10.210.154 -o smtp_bind_address6=2a01:4f8:130:9301::3 -o smtp_address_preference=any
85.10.210.154- unix - n n - - smtp -o smtp_bind_address=85.10.210.154 -o smtp_bind_address6= -o smtp_address_preference=ipv4

submission inet n - - - - smtpd -o smtpd_enforce_tls=yes -o smtpd_tls_security_level=encrypt -o smtpd_sasl_auth_enable=yes -o smtpd_client_restrictions=permit_sasl_authenticated,reject -o smtpd_sender_restrictions= -o smtpd_recipient_restrictions=permit_mynetworks,permit_sasl_authenticated,reject_unauth_destination

And my main.cf

# See /usr/share/postfix/main.cf.dist for a commented, more complete version


# Debian specific:  Specifying a file name will cause the first
# line of that file to be used as the name.  The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# TLS parameters
smtpd_tls_cert_file = /etc/postfix/postfix_default.pem
smtpd_tls_key_file = $smtpd_tls_cert_file
smtpd_use_tls = yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

myhostname = gaius.stefanshome.com
alias_maps = hash:/etc/aliases, hash:/var/spool/postfix/plesk/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = localhost.stefanshome.com, localhost, localhost.localdomain
relayhost =
mynetworks = 127.0.0.0/8 [::1]/128 85.10.210.154/32 [2a01:4f8:130:9301::3]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all
virtual_mailbox_domains = $virtual_mailbox_maps, hash:/var/spool/postfix/plesk/virtual_domains
virtual_alias_maps = $virtual_maps, hash:/var/spool/postfix/plesk/virtual
virtual_mailbox_maps = , hash:/var/spool/postfix/plesk/vmailbox
transport_maps = , hash:/var/spool/postfix/plesk/transport
smtpd_tls_security_level = may
smtp_tls_security_level = may
smtp_use_tls = no
smtpd_timeout = 3600s
smtpd_proxy_timeout = 3600s
disable_vrfy_command = yes
smtpd_sender_restrictions = check_sender_access hash:/var/spool/postfix/plesk/blacklists, permit_sasl_authenticated, check_client_access pcre:/var/spool/postfix/plesk/non_auth.re
smtpd_client_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_rbl_client ix.dnsbl.manitu.net
smtp_send_xforward_command = yes
smtpd_authorized_xforward_hosts = 127.0.0.0/8 [::1]/128
smtpd_sasl_auth_enable = yes
smtpd_recipient_restrictions = permit_mynetworks, check_client_access pcre:/var/spool/postfix/plesk/no_relay.re, permit_sasl_authenticated, reject_unauth_destination
virtual_mailbox_base = /var/qmail/mailnames
virtual_uid_maps = static:30
virtual_gid_maps = static:31
smtpd_milters = , inet:127.0.0.1:12768
non_smtpd_milters = , inet:127.0.0.1:12768
sender_dependent_default_transport_maps = hash:/var/spool/postfix/plesk/sdd_transport_maps
virtual_transport = plesk_virtual
plesk_virtual_destination_recipient_limit = 1
mailman_destination_recipient_limit = 1
virtual_mailbox_limit = 0
message_size_limit = 51200000

Best regards,

Stefan

 

[Stefan Becker]

I have activate SSL/TLS, and now it's work. Is this right?!

Stefan

 

[Lloyd_mcse]

I have activate SSL/TLS, and now it's work. Is this right?!

Stefan

Yeah, Submission Port 587 uses TLS so you must select TLS in Outlook.

 

[Stefan Becker]

Is this new? With my old configuration Debian 6 and Plesk 11.5 worked without crypto...

 

[IgorG]

JFYI, support of Debian 7.2 has been announced in MU#20. But you have Debian 7.4.

 

[Stefan Becker]

When will you support it?

Stefan