> What's the alternative? Did you make an update?

I don't know, it was about a month ago. I was trying to get the relay working so
I was making changes to the smtpd.conf file. AFAIK I was restarting smtpd after
each edit and stopped when it worked. 

Here are the diff's for my smtpd.conf from before it stopped working if it
helps:

======
/etc/mail/smtpd.conf diffs (-OLD  +NEW)
======
--- /var/backups/etc_mail_smtpd.conf.current    Fri Feb 22 01:30:23 2019
+++ /etc/mail/smtpd.conf        Fri Mar 15 20:49:37 2019
@@ -17,3 +17,5 @@
 # match from any for domain "example.org" action "local"
 match for local action "local"
 match for any action "relay"
+
+#action "relay" relay host smtp+tls://sen...@example0.co.jp:25

======
/etc/mail/smtpd.conf diffs (-OLD  +NEW)
======
--- /var/backups/etc_mail_smtpd.conf.current    Sat Mar 16 01:30:06 2019
+++ /etc/mail/smtpd.conf        Sat Mar 16 19:02:30 2019
@@ -4,13 +4,15 @@
 # See smtpd.conf(5) for more information.

 table aliases file:/etc/mail/aliases
+table secrets file:/etc/mail/secrets

 # To accept external mail, replace with: listen on all
 #
 listen on lo0

 action "local" mbox alias <aliases>
-action "relay" relay
+action "relay" user username relay host smtp+tls://my_re...@example0.co.jp:25 \
+       auth <secrets>

 # Uncomment the following to accept external mail for domain "example.org"
 #



> (Assuming Port 587 with STARTTLS.)
> Is your server IP on a blacklist? https://www.dnsbl.info/
> Can you change the password of bob?

Yes the test with Thunderbird was using STARTTLS and on port 587
The only site that has the server blacklisted is dnsbl.spfbl.net.
I changed the password once and no luck, it made no difference.

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