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I cannot receive messages from iCloud, Outlook or Gmail, but I can when I remotely telnet on port 25 or send a test message using https://www.wormly.com/test-smtp-server I receive the message in my inbox. I can also perfectly send messages to local and remote addresses.

My setup: Postfix + Dovecot + SpamAssassin + Letsencrypt

I've also disabled my UFW for testing purposes, but this doesn't seem to be the issue.

This is my Postfix main.cf:

smtpd_banner = $myhostname ESMTP

biff = no

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

readme_directory = no

compatibility_level = 2

smtpd_tls_cert_file=/etc/letsencrypt/live/thewoosh.me/fullchain.pem
smtpd_tls_key_file=/etc/letsencrypt/live/thewoosh.me/privkey.pem
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
myhostname = thewoosh.me
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = thewoosh.me, localhost.me, localhost.thewoosh.me, localhost.me, localhost.thewoosh, , localhost, localhost.localdomain
#relayhost = thewoosh.me
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
home_mailbox = Maildir/
virtual_alias_maps = hash:/etc/postfix/virtual
mailbox_command =
smtpd_sasl_auth_enable = yes
broken_sasl_auth_clients = yes
smtpd_sasl_type = dovecot
smtpd_sasl_path = private/auth
smtpd_sasl_security_options = noanonymous
smtpd_sasl_local_domain = thewoosh.me

smtpd_tls_mandatory_ciphers = medium


smtpd_helo_required = yes
smtpd_helo_restrictions =
    permit_mynetworks,
    permit_sasl_authenticated,
    reject_non_fqdn_helo_hostname,
    reject_unknown_helo_hostname

smtpd_recipient_restrictions =
    permit_mynetworks,
    permit_sasl_authenticated,
    reject_unauth_destination,
    reject_invalid_hostname,
    reject_unauth_pipelining,
    reject_non_fqdn_sender,
    reject_unknown_sender_domain,
    reject_non_fqdn_recipient,
    reject_unknown_recipient_domain,
    permit


spamassassin_destination_recipient_limit = 1
strict_rfc821_envelopes = yes
smtp_tls_security_level = encrypt

This is my master.cf:

smtp      inet  n       -       -       -       -       smtpd
  -o content_filter=spamassassin
#smtp      inet  n       -       y       -       1       postscreen
#smtpd     pass  -       -       y       -       -       smtpd
#dnsblog   unix  -       -       y       -       0       dnsblog
#tlsproxy  unix  -       -       y       -       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_tls_auth_only=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=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
smtps     inet  n       -       -       -       -       smtpd
  -o syslog_name=postfix/smtps
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$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 syslog_name=postfix/$service_name
       -o smtp_helo_timeout=30 -o smtp_connect_timeout=30
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


spamassassin unix -     n       n       -       -       pipe
    user=spamd argv=/usr/bin/spamc -f -e
    /usr/sbin/sendmail -oi -f ${sender} ${recipient}

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}

I also do not receive logs for messages sent from iCloud, Outlook or Gmail in /var/logs/mail.log, but I do when using telnet, thunderbird or wormly.

Also worth mentioning is that I have received a message from Outlook's postmaster:

Final-Recipient: rfc822;dev@thewoosh.me
Action: failed
Status: 5.4.300
Diagnostic-Code: smtp;550 5.4.300 Message expired -> 451 relay not permitted!

I've spent a few evenings trying to solve this and read a lot of threadsm but I cannot get it to work.

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  • What have you put into DNS? – Scott Aug 14 at 1:53
  • @Scott A - @ - "51.83.82.202" TXT - @ - "v=spf1 mx a -all" And some CAA entries – Woosh Aug 14 at 10:39
  • @Scott also, I've apparently got some automatic TXT record: TXT - @- " v=spf1 include:spf.efwd.registrar-servers.com ~all" – Woosh Aug 14 at 10:44

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