+1

comms3# swaks --to <email address hidden> --server forum.spinalcordmri.org -tls -p 587 
=== Trying forum.spinalcordmri.org:587...
=== Connected to forum.spinalcordmri.org.
<-  220 forum.spinalcordmri.org ESMTP OpenSMTPD
 -> EHLO localhost
<-  250-forum.spinalcordmri.org Hello localhost [46.23.90.174], pleased to meet you
<-  250-8BITMIME
<-  250-ENHANCEDSTATUSCODES
<-  250-SIZE 36700160
<-  250-DSN
<-  250-STARTTLS
<-  250 HELP
 -> STARTTLS
<-  220 2.0.0 Ready to start TLS
*** TLS startup failed (connect(): error:1400A438:SSL routines:CONNECT_CR_CERT_REQ:tlsv1 alert internal error)
*** STARTTLS attempted but failed

Causes this server-side:

root@forum:~# smtpd -d -v -Tall
[...]
31986e3ca84a940e smtp connected address=X.X.X.X host=example.org
smtp: 0x55d8d89f5240: >>> 220 forum.spinalcordmri.org ESMTP OpenSMTPD
smtp: 0x55d8d89f5240: IO_LOWAT <io:0x55d8d89f6530 fd=16 to=300000 fl=W ib=0 ob=0>
smtp: 0x55d8d89f5240: IO_DATAIN <io:0x55d8d89f6530 fd=16 to=300000 fl=R ib=16 ob=0>
smtp: 0x55d8d89f5240: <<< EHLO localhost
smtp: 0x55d8d89f5240: STATE_CONNECTED -> STATE_HELO
smtp: 0x55d8d89f5240: >>> 250-forum.spinalcordmri.org Hello localhost [X.X.X.X], pleased to meet you
smtp: 0x55d8d89f5240: >>> 250-8BITMIME
smtp: 0x55d8d89f5240: >>> 250-ENHANCEDSTATUSCODES
smtp: 0x55d8d89f5240: >>> 250-SIZE 36700160
smtp: 0x55d8d89f5240: >>> 250-DSN
smtp: 0x55d8d89f5240: >>> 250-STARTTLS
smtp: 0x55d8d89f5240: >>> 250 HELP
smtp: 0x55d8d89f5240: IO_LOWAT <io:0x55d8d89f6530 fd=16 to=300000 fl=W ib=0 ob=0>
smtp: 0x55d8d89f5240: IO_DATAIN <io:0x55d8d89f6530 fd=16 to=300000 fl=R ib=10 ob=0>
smtp: 0x55d8d89f5240: <<< STARTTLS
smtp: 0x55d8d89f5240: >>> 220 2.0.0 Ready to start TLS
smtp: 0x55d8d89f5240: STATE_HELO -> STATE_TLS
smtp: 0x55d8d89f5240: IO_LOWAT <io:0x55d8d89f6530 fd=16 to=300000 fl=W ib=0 ob=0>
mproc: pony -> lka : 11 IMSG_CERT_INIT
imsg: lka <- pony: IMSG_CERT_INIT (len=11)
debug: looking up pki "kousu"
mproc: lka -> pony: realloc 128 -> 8192
mproc: lka -> pony : 5608 IMSG_CERT_INIT
imsg: pony <- lka: IMSG_CERT_INIT (len=5608)
debug: session_start_ssl: switching to SSL
debug: pony: rsae_priv_enc
debug: pony: rsae_bn_mod_exp
debug: SSL library error: io_dispatch_accept_tls:SSL_accept: error:020000B3:rsa routines::missing private key
debug: SSL library error: io_dispatch_accept_tls:SSL_accept: error:1C880004:Provider routines::RSA lib
debug: SSL library error: io_dispatch_accept_tls:SSL_accept: error:0A080006:SSL routines::EVP lib
smtp: 0x55d8d89f5240: IO_ERROR <io:0x55d8d89f6530 fd=16 to=300000 fl=R tls=TLSv1.3:TLS_AES_256_GCM_SHA384:256 ib=0 ob=0>
31986e3ca84a940e smtp disconnected reason="io-error: error:0A080006:SSL routines::EVP lib"


With

root@forum:/var/discourse# apt policy opensmtpd
opensmtpd:
  Installed: 6.8.0p2-4build1
  Candidate: 6.8.0p2-4build1
  Version table:
 *** 6.8.0p2-4build1 500
        500 http://mirrors.digitalocean.com/ubuntu jammy/universe amd64 Packages
        100 /var/lib/dpkg/status
root@forum:/var/discourse# apt policy openssl
openssl:
  Installed: 3.0.2-0ubuntu1.6
  Candidate: 3.0.2-0ubuntu1.6
  Version table:
 *** 3.0.2-0ubuntu1.6 500
        500 http://mirrors.digitalocean.com/ubuntu jammy-updates/main amd64 Packages
        500 http://security.ubuntu.com/ubuntu jammy-security/main amd64 Packages
        100 /var/lib/dpkg/status
     3.0.2-0ubuntu1 500
        500 http://mirrors.digitalocean.com/ubuntu jammy/main amd64 Packages