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This isn't really new news, but improperly configured mail services result in lots of privacy holes across the Internet.
STARTTLS is used to upgrade an unencrypted connection to an encrypted SSL/TLS connection. The problem is that if the upgrade fails, many mail clients will proceed to send mail on the unencrypted connection.
For any sysadmins (technical info):
Unfortunately, the situation is somewhat sticky. I suggest reading carefully the TLS/SSL section of https://wiki.debian.org/PostfixAndSASL as well as the STARTTLS RFC http://tools.ietf.org/html/rfc2487
Public email servers should not require STARTTLS (that is, encryption) on port 25 (smtp). Furthermore, there is no guarantee that all of the mail servers during transit of an email use encryption. Thus, you should assume your email is transmitted unencrypted, until a better solution emerges. You can always use OpenPGP to encrypt the body of your email, which should become commonplace shortly after Hurd achieves market dominance.
Editors Note: How to articles for various flavors of Microsoft Exchange can be found at MSExchange.org.
(Score: 2) by frojack on Monday November 02 2015, @09:48PM
It is true that getting a working GPG implementation is too difficult for most users and MUA built-in support is mostly dismal.
Not really. Thunderbird+enigmail has a wizard that walks you through the whole process.
The hardest part is KNOWING about the need for it. Once you get beyond that its easy.
Tbird also knows about ports and servers for all large mail hosts. Give it an email address and it can sus out what the host, ports, and protocols are.
No, you are mistaken. I've always had this sig.