Gmail Still Says My Postfix/Dovecot Emails Are Insecure

When I send an email using my Outgoing Server (SMTP) in Thunderbird to my personal Gmail account using SSL/TLS, using the self-signed "Snakeoil" certificate and private key and the CAFile ca-certificates.crt, it shows up in Gmail with an "unlocked" icon and it says:

"encryption: richardkarlschultz.com did not encrypt this message"

How do I check that this is accurate and that it's being encrypted appropriately? Could there be something else going on here?

4 Replies

Another thread about this from just a few days ago…

https://forum.linode.com/viewtopic.php?f=11&t=14007

Awesome! Adding the following to /etc/postfix/main.cf fixed it!

smtpd_tls_security_level = may
smtp_tls_security_level = may

Thank you!

Also, I learned you can verify TLS encryption in the other direction (from Gmail to your mail server) by adding the following lines to /etc/postfox/main.cf:

smtpd_tls_received_header = yes
smtpd_tls_loglevel = 1

This doesn't actually change how encryption happens, it just adds a line to the received email header in your mail server to help you verify TLS is being used. It can be safey removed again once you are assured it is working. These header lines aren't enabled by default.

Source: https://ubuntuforums.org/archive/index. … 93222.html">https://ubuntuforums.org/archive/index.php/t-493222.html

That's an interesting find rschultz. Email used to be a lot easier. :)

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