I just got bit by this, too. I recently set up a Debian Postfix server and manually verified that the server was offering STARTTLS with the correct cert. It was working correctly, so I assumed TLS working as expected out-of-the-box. A month later, a friend notified me that Gmail warned about my mail being sent unencrypted.

This asymmetry of defaults between incoming and outgoing mail is surprising and silently guides users towards insecure configurations.

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