> On my server (OpenBSD 6.9 + OpenSMTPD 6.9.0) this message appears since 
> I have upgraded to OpenBSD 6.9.
> 
> ...
> 
> When I test the server connection manually with the OpenSSL command line 
> utility, both certificates will
> be shown.

Are there multiple domains involved in your configuration? As smtpd was ported 
to libtls, there were major configuration changes concerning the pki listener 
option. Also, are there any more detailed tls options in your listener config? 
Because looking at the source code [1] it seems that tls_peer_cert_provided is 
returning 0.

[1] 
https://github.com/OpenSMTPD/OpenSMTPD/blob/9e195177ab8354f188d156a82b11e7d38e517bc7/usr.sbin/smtpd/mta_session.c#L1606

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