I have an OpenBSD 6.1 box set up with OpenSMTPD and Dovecot on Vultr (a 
VPS provider).

This machine is intended for use as my primary mail server.  I have a Let’s 
Encrypt certificate installed and declared in the smtpd.conf file like so:

#       $OpenBSD: smtpd.conf,v 1.9 2016/05/03 18:43:45 jung Exp $

# This is the smtpd server system-wide configuration file.
# See smtpd.conf(5) for more information.

# pki setup (Define TLS Certificates for host names)

pki pfc-consulting.com certificate "/etc/ssl/pfc-consulting.com.crt"
pki pfc-consulting.com key "/etc/ssl/private/pfc-consulting.com.key"

# tables setup

table aliases file:/etc/mail/aliases
table domains file:/etc/mail/domains
table passwd passwd:/etc/mail/passwd
table virtuals file:/etc/mail/virtuals

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

# listen ports setup

listen on lo0
listen on egress port 25 tls-require pki pfc-consulting.com auth <passwd>
listen on egress port 587 tls-require pki pfc-consulting.com auth <passwd>

# special case for gmail to avoid ipv6 here
limit mta for domain gmail.com inet4

# allow local messages
accept from local for local alias <aliases> deliver to lmtp "/var/dovecot/lmtp" 
rcpt-to

# allow virtual domains
accept from any for domain <domains> virtual <virtuals> deliver to lmtp 
"/var/dovecot/lmtp" rcpt-to

# allow outgoing mails
accept from local for any relay

I have the system set up for IMAP only (no POP3) and I have sent and received 
email from my computer at home to this machine.

(as an aside, I have MX and spf records defined in DNS)

I can send and receive mail ok using Apple Mail on my mac.  Thunderbird is 
another story…  I am warned when I set up the account that SMTP is NOT 
encrypted.

This has driven me batty all week.  My Google-Foo fails me and reading through 
my Dovecot book and smtpd man pages have not enlightened me as to why this is 
not using TLS.

When I telnet to the machine on port 587 and issue the EHLO command, STARTTLS 
does appear in the response.  Also, OpenSMTPD shows when I type the help 
command.

issuing a Mail command comes back with the response that STARTTLS must be done 
first.

Can someone clue me in on what I might be missing?

Thanks in advance for your help!

— Paul.

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