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I just set up a mail server with Postfix, Dovecot and Mysql. I can sent/receive emails to/from Gmail, Hotmail etc. but mails sent from a specific Microsoft Mail Exchange Server (using Outlook) bounces from my server. Strangely i can send mails from my server to this Microsoft server without any problems but vice-versa is not happening. I even tried to add this server's IP to "mynetworks" on Postfix but no luck so far. Also nothing appears on the mail.log or mail.err

Here is the bounce details:

Delivery has failed to these recipients or groups:

'[email protected]' ([email protected]) <mailto:[email protected]> 
The e-mail address you entered couldn't be found. Please check the recipient's e-mail address and try to resend the message. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:
Generating server: xxx.MSserver.tdl

[email protected]
#550 5.1.1 RESOLVER.ADR.RecipNotFound; not found ##

Original message headers:
Received: from xxx.MSserver.tdl ([xxx:xxx]) by
 xxx.MSserver.tdl ([xx:xxx]) with mapi id
 14.03.0361.001; Sun, 5 Nov 2017 11:09:02 +0100
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: "[email protected]" <[email protected]>
To: "'[email protected]'" <[email protected]>
Subject: adsdsadsaads
Thread-Topic: adsdsadsaads
Thread-Index: AdNWHhlzozN+mupPTPWC2nI6WYXmdA==
Date: Sun, 5 Nov 2017 11:09:01 +0100
Message-ID: <[email protected]>
Accept-Language: en-US, de-DE
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator: <[email protected]>
MIME-Version: 1.0
X-Originating-IP: [xxxxx]

Here is my main.cf:

smtpd_banner = $myhostname ESMTP $mail_name (xxx)
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/letsencrypt/live/xxxxx.com/fullchain.pem
smtpd_tls_key_file=/etc/letsencrypt/live/xxxxx.com/privkey.pem
smtpd_use_tls=yes
smtpd_tls_auth_only = yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_tls_CAfile = /etc/letsencrypt/live/xxx.com/fullchain.pem
smtpd_tls_security_level = encrypt
smtp_tls_security_level = encrypt
smtp_tls_CAfile = /etc/letsencrypt/live/xxx.com/fullchain.pem
smtp_tls_cert_file = /etc/letsencrypt/live/xxx.com/fullchain.pem
smtp_tls_key_file = /etc/letsencrypt/live/xxx.com/privkey.pem
smtp_use_tls = yes
smtpd_tls_received_header = yes
smtpd_tls_ask_ccert = yes
smtpd_tls_loglevel = 4


smtpd_sasl_type = dovecot
smtpd_sasl_path = private/auth
smtpd_sasl_auth_enable = yes
smtpd_recipient_restrictions =
        permit_sasl_authenticated,
        permit_mynetworks,
        reject_unauth_destination


virtual_mailbox_base = /var/vmail
virtual_transport = lmtp:unix:private/dovecot-lmtp
virtual_mailbox_domains = mysql:/etc/postfix/mysql-virtual-mailbox-domains.cf
virtual_mailbox_maps = mysql:/etc/postfix/mysql-virtual-mailbox-maps.cf
virtual_alias_maps = mysql:/etc/postfix/mysql-virtual-alias-maps.cf

# 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 = defer_unauth_destination

mydomain = mydomain.com
myhostname = mail.mydomain.com
alias_maps = hash:/etc/aliases, nis:mail.aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = localhost
#relayhost = 
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all

Here is my master.cf

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 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       -       y       -       -       smtpd
  -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       -       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}

policy-spf  unix  -       n       n       -       -       spawn
     user=nobody argv=/usr/bin/policyd-spf

1 Answer 1

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You mentioned that you've just set up the mail server - does that include updating the DNS records? If the DNS records have been changed recently, there's a chance that the new records haven't fully propagated yet.

You could confirm this with a tool like https://dnschecker.org which shows DNS propagation across different servers.

This would also be supported by the #550 5.1.1 RESOLVER.ADR.RecipNotFound; error that you're getting - more information on that here. That page also mentions checking for typos in the e-mail address you're sending to.

If DNS caching is the cause, you'll just have to wait until the Exchange server's DNS records are updated.

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  • Hi @ishihoya . Thanks for the reply. I've solved the problem. I figured out that both domains were on the same namespace and hosting provider had some old configurations saved in their system. I contact them to fix this and they did so. It's all working now.
    – Rasko
    Nov 6, 2017 at 16:23

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