Thank you for your input Archange,

Please see below


On Sun, 20 Sep 2020 03:20:49 +0400
Archange <archa...@activis.me> wrote:

> ...
> 
> Just to check something, how are you identifying to the server? Your
> current setup implies it is using a system user and password, is that
> the case?


This is correct. 


> Other than that, you’re configuration looks very similar to mine. The
> other difference I can see is that I know use the more compact `from
> auth` instead of `from any auth`, and I seem to remember my former
> syntax to be `auth from any` and not `from any auth`, so maybe you could
> try one of my two versions?



I actually tried both but the error I am getting didn't change. "550 Invalid 
recipient: <recipi...@gmail.com>"



And on sterr "smtp_cert_verify_cb: no-client-cert
no rule matched"

I wonder if this is somehow related to ipv6. It is a wild guess but I cannot 
explain why there wouldn't be any client certificate, assuming the client is 
gmail in this case.

Hakan



> Le 20/09/2020 à 02:39, Hakan E. Duran a écrit :
> > I played around a little bit more and was able to get this error message 
> > with the command `doas smtpd -d -T rules -v`, which may be a little more 
> > informative:
> >
> >
> >
> >
> > 798b98fc3686a31c smtp connected address=111.11.1.111 
> > host=111-11-1-111.client.something.com
> > debug: looking up pki "mail.name.com"
> > debug: session_start_ssl: switching to SSL
> > debug: pony: rsae_priv_enc
> > 798b98fc3686a31c smtp tls ciphers=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256
> > smtp: 0x184169a23000: smtp_cert_verify_cb: no-client-cert
> > no rule matched
> > 798b98fc3686a31c smtp failed-command command="RCPT 
> > TO:<recipi...@gmail.com>" result="550 Invalid recipient: 
> > <recipi...@gmail.com>"
> > 798b98fc3686a31c smtp disconnected reason=disconnect
> >
> > Please notice the more informative line stating: *smtp_cert_verify_cb: 
> > no-client-cert*
> >
> > The certificate of concern here cannot be the server's certificate, because 
> > they are in the right place where smtpd.conf points to. It cannot possibly 
> > be gmail's certificate either, but that is the client, isn't it? It feels 
> > like I am hitting a bug here.
> >
> > Hakan
> >
> >
> >
> > On Sat, 19 Sep 2020 12:35:41 -0500
> > "Hakan E. Duran" <ehakandu...@gmail.com> wrote:
> >
> >> 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:<recipi...@gmail.com>" result="550 Invalid recipient: 
> >> <recipi...@gmail.com>"
> >> 99d03ce4cb968916 smtp disconnected reason=disconnect
> >>
> >> Thanks again for brainstorming with me.
> >>
> >> Hakan
> >>
> >>
> >> On Sat, 19 Sep 2020 12:13:06 +0000
> >> br...@sally.org.il 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" <ehakandu...@gmail.com 
> >>> (mailto:ehakandu...@gmail.com?to=%22Ey%C3%BCp%20Hakan%20Duran%22%20<ehakandu...@gmail.com>)>
> >>>  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: 
> >>> <recipi...@gmail.com (mailto:recipi...@gmail.com)>"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:<recipi...@gmail.com (mailto:recipi...@gmail.com)>" result="550 
> >>> Invalid recipient: <recipi...@gmail.com (mailto:recipi...@gmail.com)>"
> >>> 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 <ehakandu...@gmail.com>
> >


-- 
Hakan E. Duran <ehakandu...@gmail.com>

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