Thank you so much Bryan for your reply. I tried doing it and received a 
response indicating no rule matched. What am I missing? Here is the complete 
output of `doas smtpd -d -T rules`:




99d03ce4cb968916 smtp connected address=111.11.1.111 
host=111-11-1-111.client.something.com
99d03ce4cb968916 smtp tls ciphers=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256
no rule matched
99d03ce4cb968916 smtp failed-command command="RCPT TO:<[email protected]>" 
result="550 Invalid recipient: <[email protected]>"
99d03ce4cb968916 smtp disconnected reason=disconnect

Thanks again for brainstorming with me.

Hakan


On Sat, 19 Sep 2020 12:13:06 +0000
[email protected] wrote:

> Hello,
> 
> Maybe I'm crazy but do you want to trace the rules instead of the lookup?
> 
> V/r,
> Bryan
> September 18, 2020 11:30 PM, "Eyüp Hakan Duran" <[email protected] 
> (mailto:[email protected]?to=%22Ey%C3%BCp%20Hakan%20Duran%22%20<[email protected]>)>
>  wrote:
> Dear all,
> 
> I am aware that this is most probably a silly oversight on my part but I 
> would really appreciate gentle guidance to the right direction to overcome 
> this impasse. I truly appreciate your time.
> 
> I rented a VPS, installed OpenBSD 6.7 and set up a mail server as described 
> here 
> (https://poolp.org/posts/2019-09-14/setting-up-a-mail-server-with-opensmtpd-dovecot-and-rspamd/).
>  I double and triple checked all the settings, including MX records, reverse 
> DNS, etc. and confirmed everything is resolving. Here is my redacted 
> smtpd.conf:
> 
> --------
> pki mail.name.com (http://mail.name.com) cert 
> "/etc/ssl/mail.name.com.fullchain.pem"
> pki mail.name.com (http://mail.name.com) key 
> "/etc/ssl/private/mail.name.com.key"
> 
> filter check_dyndns phase connect match rdns regex { '.*.dyn..*', '.*.dsl..*' 
> } junk
> 
> filter check_rdns phase connect match !rdns junk
> 
> filter check_fcrdns phase connect match !fcrdns junk
> 
> filter senderscore 
> proc-exec "filter-senderscore -junkBelow 70 -slowFactor 5000"
> 
> filter rspamd proc-exec "filter-rspamd"
> table aliases file:/etc/mail/aliases
> 
> listen on all tls pki mail.kumru.club 
> filter { check_dyndns, check_rdns, check_fcrdns, senderscore, rspamd }
> 
> listen on all port submission tls-require pki mail.name.com 
> (http://mail.name.com) auth filter rspamd
> 
> action "local_mail" maildir junk alias <aliases>
> action "outbound" relay helo mail.name.com (http://mail.name.com)
> 
> match from any for domain "name.com (http://name.com)" action "local_mail"
> match for local action "local_mail"
> 
> match from any auth for any action "outbound"
> match for any action "outbound"
> 
> -----------------------
> 
> There is no problem in sending email from within the VPS. Unfortunately every 
> time I try to send an email from my local computer and try to use the smtpd 
> server in VPS as a relay, I get a "550 Invalid recipient: 
> <[email protected] (mailto:[email protected])>"error.
> 
> Here is the output of `doas smtpd -d -T lookup` (redacted):
> 
> ------------------------
> info: OpenSMTPD 6.7.0 starting
> 24875097a9b2d457 smtp connected address=111.11.1.111 
> host=111-11-1-111.client.something.com 
> (http://111-11-1-111.client.something.com)
> lookup: match "111-11-1-111.client.something.com 
> (http://111-11-1-111.client.something.com)" as REGEX in table 
> static:<dynamic:0> -> false
> 24875097a9b2d457 smtp tls ciphers=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256
> lookup: match "111.11.1.111" as NETADDR in table static:<anyhost> -> true
> lookup: match "gmail.com (http://gmail.com)" as DOMAIN in table 
> static:<dynamic:1> -> false
> lookup: match "111.11.1.111" as NETADDR in table static:<localhost> -> false
> lookup: match "111.11.1.111" as NETADDR in table static:<anyhost> -> true
> lookup: match "gmail.com (http://gmail.com)" as DOMAIN in table 
> static:<anydestination> -> true
> lookup: match "111.11.1.111" as NETADDR in table static:<localhost> -> false
> 24875097a9b2d457 smtp failed-command command="RCPT TO:<[email protected] 
> (mailto:[email protected])>" result="550 Invalid recipient: 
> <[email protected] (mailto:[email protected])>"
> 24875097a9b2d457 smtp disconnected reason=disconnect
> ------------------------
> 
> It appears to my untrained and careless eyes that the sender/recipient 
> combination fits to the "outbound" ruleset and therefore should be relayed to 
> gmail's smtp; however, it is clearly not the case. I will truly appreciate 
> any pointers to solve this issue.
> 
> Regards,
> 
> Hakan Duran


-- 
Hakan E. Duran <[email protected]>

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