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Operating system: Ubuntu 16.04

Software used for its purpose: LAMP, Dovecot, Postfix, Roundcube, Amavis, ClamAV and SpamAssassin

I configured mail sever with following tutorial:

https://www.exratione.com/2016/05/a-mailserver-on-ubuntu-16-04-postfix-dovecot-mysql/

When I send email from gmail to postfix, it gets to its mailbox. When I send from postfix to anyone, mail goes trough. Problem is when email from office.com is sent to it and it gets stuck with status pending. So message is received using TLS1.2, it gets submitted, but then its deferred. Message trace with error from office355 is (censored tho):

Reason: [{LED=454 4.7.1 <example@domain.org>: Relay access denied};{MSG=};{FQDN=xxx.xxx.xxx.xxx};{IP=xxx.xxx.xxx.xxx};{LRT=6/19/2018 12:28:55 PM}]. OutboundProxyTargetIP: xxx.xxx.xxx.xxx.

So its just gets stuck and never delivered.

Here is main.cf file:

# 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 (Ubuntu)
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/ssl/certs/ssl-cert-snakeoil.pem
#smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
#smtpd_tls_cert_file = /etc/ssl/certs/mailcert.pem
#smtpd_tls_key_file = /etc/ssl/private/mail.key
smtpd_tls_cert_file =  /etc/letsencrypt/live/postfix.civicatalyst.org/fullchain.pem
smtpd_tls_key_file =  /etc/letsencrypt/live/postfix.civicatalyst.org/privkey.pem
smtpd_use_tls=yes
smtp_tls_security_level = may

#smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
#smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache
#smtp_tls_CApath = /etc/ssl/certs
#smtpd_tls_CApath = /etc/ssl/certs



smtpd_tls_mandatory_protocols=!SSLv2,!SSLv3
smtp_tls_note_starttls_offer = yes
smtpd_tls_loglevel = 1
smtpd_tls_received_header = yes
smtpd_tls_session_cache_timeout = 3600s
tls_random_source = dev:/dev/urandom
smtpd_tls_exclude_ciphers = aNULL, eNULL, EXPORT, DES, RC4, MD5, PSK, aECDH, EDH-DSS-DES-CBC3-SHA, EDH-RSA-DES-CDC3-SHA, KRB5-DE5, CBC3-SHA
smtpd_tls_dh1024_param_file = /etc/ssl/private/dhparams.pem

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

#smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
#myhostname = localhost.kcbhng4ypoeu5dqy2dcukxqy4e.ax.internal.cloudapp.net
myhostname = postfix.civicatalyst.org
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
#myorigin = /etc/mailname
myorigin = /etc/hostname
#mydestination = $myhostname, postfix.civicatalyst.org, localhost, localhost.localdomain, localhost
mydestination =
relayhost =
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_command = procmail -a "$EXTENSION"
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
#inet_interfaces = loopback-only
inet_protocols = all
mynetworks_style = host

# This specifies where the virtual mailbox folders will be located.
virtual_mailbox_base = /var/vmail
# This is for the mailbox location for each user. The domainaliases
# map allows us to make use of Postfix Admin's domain alias feature.
virtual_mailbox_maps = mysql:/etc/postfix/mysql_virtual_mailbox_maps.cf, mysql:/etc/postfix/mysql_virtual_mailbox_domainaliases_maps.cf
# and their user id
virtual_uid_maps = static:150
# and group id
virtual_gid_maps = static:8
# This is for aliases. The domainaliases map allows us to make
# use of Postfix Admin's domain alias feature.
virtual_alias_maps = mysql:/etc/postfix/mysql_virtual_alias_maps.cf, mysql:/etc/postfix/mysql_virtual_alias_domainaliases_maps.cf
# This is for domain lookups.
virtual_mailbox_domains = mysql:/etc/postfix/mysql_virtual_domains_maps.cf
# Used in conjunction with reject_authenticated_sender_login_mismatch to
# verify that the sender is sending with their own address, or with one
# of the aliases mapped to that address.
smtpd_sender_login_maps = mysql:/etc/postfix/mysql_virtual_sender_login_maps.cf

# ---------------------------------
# Integration with other packages
# ---------------------------------------

# Tell postfix to hand off mail to the definition for dovecot in master.cf
virtual_transport = dovecot
dovecot_destination_recipient_limit = 1

# Use amavis for virus and spam scanning
content_filter = amavis:[127.0.0.1]:10024

# Settings for checking SPF to cut down spam.
policy-spf_time_limit = 3600s

# ---------------------------------
# Header manipulation
# --------------------------------------

# Getting rid of unwanted headers. See: https://posluns.com/guides/header-removal/
header_checks = regexp:/etc/postfix/header_checks
# getting rid of x-original-to
enable_original_recipient = no



# ---------------------------------
# SASL parameters
# ---------------------------------

# Use Dovecot to authenticate.
smtpd_sasl_type = dovecot
# Referring to /var/spool/postfix/private/auth
smtpd_sasl_path = private/auth
smtpd_sasl_auth_enable = yes
broken_sasl_auth_clients = yes
smtpd_sasl_security_options = noanonymous
smtpd_sasl_local_domain =
smtpd_sasl_authenticated_header = yes


# ---------------------------------
# SMTPD parameters
# ---------------------------------

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h
# will it be a permanent error or temporary
unknown_local_recipient_reject_code = 450
# how long to keep message on queue before return as failed.
maximal_queue_lifetime = 7d
# max and min time in seconds between retries if connection failed
minimal_backoff_time = 1000s
maximal_backoff_time = 8000s
# how long to wait when servers connect before receiving rest of data
smtp_helo_timeout = 60s
# how many address can be used in one message.
# effective stopper to mass spammers, accidental copy in whole address list
# but may restrict intentional mail shots.
smtpd_recipient_limit = 16
# how many error before back off.
smtpd_soft_error_limit = 3
# how many max errors before blocking it.
smtpd_hard_error_limit = 12

# This next set are important for determining who can send mail and relay mail
# to other servers. It is very important to get this right - accidentally producing
# an open relay that allows unauthenticated sending of mail is a Very Bad Thing.
#
# You are encouraged to read up on what exactly each of these options accomplish.

# Requirements for the HELO statement
smtpd_helo_restrictions = permit_mynetworks, warn_if_reject reject_non_fqdn_hostname, reject_invalid_hostname, permit

# Requirements for the sender details. Note that the order matters.
# E.g. see http://jimsun.linxnet.com/misc/restriction_order_prelim-03.txt

smtpd_sender_restrictions = permit_mynetworks, reject_authenticated_sender_login_mismatch, permit_sasl_authenticated, warn_if_reject reject_non_fqdn_sender, reject_unknown_sender_domain, reject_unauth_pipelining, permit
# Requirements for the connecting server

smtpd_client_restrictions = reject_rbl_client sbl.spamhaus.org, reject_rbl_client blackholes.easynet.nl
# Requirement for the recipient address. Note that the entry for
# "check_policy_service inet:127.0.0.1:10023" enables Postgrey.

smtpd_recipient_restrictions = reject_unauth_pipelining, permit_mynetworks, permit_sasl_authenticated, reject_non_fqdn_recipient, reject_unknown_recipient_domain, reject_unauth_destination, check_policy_service unix:private/policy-spf, check_policy_service inet:127.0.0.1:10023, permit
smtpd_data_restrictions = reject_unauth_pipelining

# This is a new option as of Postfix 2.10, and is required in addition to
# smtpd_recipient_restrictions for things to work properly in this setup.

smtpd_relay_restrictions = reject_unauth_pipelining, permit_mynetworks, permit_sasl_authenticated, reject_non_fqdn_recipient, reject_unknown_recipient_domain, reject_unauth_destination, check_policy_service unix:private/policy-spf, check_policy_service inet:127.0.0.1:10023, permit

# require proper helo at connections
smtpd_helo_required = yes
# waste spammers time before rejecting them
smtpd_delay_reject = yes
disable_vrfy_command = yes


milter_protocol = 6
milter_default_action = accept
smtpd_milters = inet:localhost:12345
non_smtpd_milters = inet:localhost:12345

Here is 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" or
# on-line: http://www.postfix.org/master.5.html).
#
# Do not forget to execute "postfix reload" after editing this file.
#
# ==========================================================================
# service type  private unpriv  chroot  wakeup  maxproc command + args
#               (yes)   (yes)   (no)    (never) (100)
# ==========================================================================
smtp      inet  n       -       y       -       -       smtpd
#smtp      inet  n       -       y       -       1       postscreen
#smtpd     pass  -       -       y       -       -       smtpd
#dnsblog   unix  -       -       y       -       0       dnsblog
#tlsproxy  unix  -       -       y       -       0       tlsproxy
#submission inet n       -       y       -       -       smtpd
#  -o syslog_name=postfix/submission
#  -o smtpd_tls_security_level=encrypt
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$mua_client_restrictions
#  -o smtpd_helo_restrictions=$mua_helo_restrictions
#  -o smtpd_sender_restrictions=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#smtps     inet  n       -       y       -       -       smtpd
#  -o syslog_name=postfix/smtps
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$mua_client_restrictions
#  -o smtpd_helo_restrictions=$mua_helo_restrictions
#  -o smtpd_sender_restrictions=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#628       inet  n       -       y       -       -       qmqpd
pickup    unix  n       -       y       60      1       pickup
cleanup   unix  n       -       y       -       0       cleanup
qmgr      unix  n       -       n       300     1       qmgr
#qmgr     unix  n       -       n       300     1       oqmgr
tlsmgr    unix  -       -       y       1000?   1       tlsmgr
rewrite   unix  -       -       y       -       -       trivial-rewrite
bounce    unix  -       -       y       -       0       bounce
defer     unix  -       -       y       -       0       bounce
trace     unix  -       -       y       -       0       bounce
verify    unix  -       -       y       -       1       verify
flush     unix  n       -       y       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       y       -       -       smtp
relay     unix  -       -       y       -       -       smtp
#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
showq     unix  n       -       y       -       -       showq
error     unix  -       -       y       -       -       error
retry     unix  -       -       y       -       -       error
discard   unix  -       -       y       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       y       -       -       lmtp
anvil     unix  -       -       y       -       1       anvil
scache    unix  -       -       y       -       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=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py
  ${nexthop} ${user}


# SMTP with TLS on port 587. Currently commented.
submission inet n       -       y       -       -       smtpd
  -o syslog_name=postfix/submission
  -o smtpd_tls_security_level=encrypt
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_enforce_tls=yes
  -o smtpd_client_restrictions=permit_sasl_authenticated,reject_unauth_destination,reject
  -o smtpd_sasl_tls_security_options=noanonymous


# SMTP over SSL on port 465.
#smtps     inet  n       -       y       -       -       smtpd
#  -o syslog_name=postfix/smtps
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_tls_auth_only=yes
#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject_unauth_destination,reject
#  -o smtpd_sasl_security_options=noanonymous,noplaintext
#  -o smtpd_sasl_tls_security_options=noanonymous

# The next two entries integrate with Amavis for anti-virus/spam checks.
amavis      unix    -       -       y       -       3       smtp
  -o smtp_data_done_timeout=1200
  -o smtp_send_xforward_command=yes
  -o disable_dns_lookups=yes
  -o max_use=20
127.0.0.1:10025 inet    n       -       y       -       -       smtpd
  -o content_filter=
  -o local_recipient_maps=
  -o relay_recipient_maps=
  -o smtpd_restriction_classes=
  -o smtpd_delay_reject=no
  -o smtpd_client_restrictions=permit_mynetworks,reject
  -o smtpd_helo_restrictions=
  -o smtpd_sender_restrictions=
  -o smtpd_recipient_restrictions=permit_mynetworks,reject
  -o smtpd_data_restrictions=reject_unauth_pipelining
  -o smtpd_end_of_data_restrictions=
  -o mynetworks=127.0.0.0/8
  -o smtpd_error_sleep_time=0
  -o smtpd_soft_error_limit=1001
  -o smtpd_hard_error_limit=1000
  -o smtpd_client_connection_count_limit=0
  -o smtpd_client_connection_rate_limit=0
  -o receive_override_options=no_header_body_checks,no_unknown_recipient_checks,no_milters

# Integration with Dovecot - hand mail over to it for local delivery, and
# run the process under the vmail user and mail group.
dovecot      unix   -        n      n       -       -   pipe
  flags=DRhu user=vmail:mail argv=/usr/lib/dovecot/dovecot-lda -d $(recipient)

# Integration with the SPF check package.
policy-spf  unix  -       n       n       -       -       spawn
     user=nobody argv=/usr/bin/policyd-spf

127.0.0.1:25025 inet    n       -       -       -       -       smtpd
 -o smtpd_milters=

If there is anything needed, such as dovecot confs or any other software used in tutorial let me know. I think its mostly vanilla from the tutorial itself, all configurations.

I did check if domain is blacklisted and requested reset for mailbox and IP itself, it wasn't.

Thanks to all that take time to read and respond,

12
  • "Relay access denied". This implies that the addresses in MAIL FROM and RCPT TO are both for domains not hosted on your server. Are you sure you're sending an email from O365 using the correct from address? not using any weird aliases? Jun 19 '18 at 17:26
  • Only added aliases that I have are: @example.com info@example.com ( catchall for all mailboxes that doesn't exist to get into the info mailbox). We only have 2 mailboxes: info@example.com bounce@example.com info has alias for bounce mailbox to forward all emails to it, we are using this for bounce processing for our application. Jun 20 '18 at 8:44
  • Just checked all different emails I had, doesn't work with any client. DNS records that are there are, MX record for domain that points to mail server (postfix.example.com) domain, SPF, DKIM and DMARC (set to none tho). RDNS is set to point to domain name postfix.example.com. Any flaw with that maybe?? Should I use a wildcard for RDNS, like *.example.com? Jun 20 '18 at 8:58
  • 1
    can you post the complete log message containing the error, and the two or three relevant messages above it? (mask any personal info of course) Jun 20 '18 at 11:04
  • 1
    Could it be a filter? you have a milter on 25025, what is it? Jun 20 '18 at 12:04

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