Hi,

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?

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?

Regards,
Archange

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:<[email protected]>" 
> result="550 Invalid recipient: <[email protected]>"
> 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" <[email protected]> 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:<[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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