Outlook Pop Up for SSL

That’s not a Letsencrypt certificate.

Are there other instances running?

There must be urls with that certificate so you can find the running instance.

No other instances.

root@mail1:~# sudo grep -r /etc/ssl/private /etc
/etc/postfix/main.cf:#smtpd_tls_cert_file = /etc/ssl/private/fullchain.pem
/etc/postfix/main.cf:smtpd_tls_cert_file = /etc/ssl/private/fullchain.pem
/etc/postfix/main.cf:#smtpd_tls_key_file = /etc/ssl/private/privkey.pem
/etc/postfix/main.cf:smtpd_tls_key_file = /etc/ssl/private/privkey.pem
/etc/postfix/main.cf:#smtpd_tls_CAfile = /etc/ssl/private/fullchain.pem
/etc/apache2/sites-available/default-ssl.conf: SSLCertificateKeyFile /etc/ssl/private/ssl-cert-snakeoil.key

That's not

/etc/letsencrypt/live/mail.domain.tld/fullchain.pem

I did change it for testing purposes. I expected that maybe postfix user is not able to read it from /etc/letsencrypt/live/mail.domain.tld/fullchain.pem. So I copied the SSL files to /etc/ssl/private/ just to test. Still the same results.

In Outlook, are you using POP, IMAP, or RPC/HTTPs to connect to your mail server?

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