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Do Not Rely on STARTTLS to Automatically Encrypt Your Sensitive E-mails

posted by martyb on Monday November 02 2015, @01:19PM   Printer-friendly
from the ask-and-ye-might-not-receive dept.

darkfeline writes:

http://arstechnica.com/security/2015/10/dont-count-on-starttls-to-automatically-encrypt-your-sensitive-e-mails/

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.

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  • (Score: 0) by Anonymous Coward on Monday November 02 2015, @03:06PM

    by Anonymous Coward on Monday November 02 2015, @03:06PM (#257522)

    Email has always been like this. Email is NOT secure. It can be read en-route by any number of points. If you want to send secure information, encrypt it separately and DON'T EMAIL THE KEY.

    That this is inconvenient, e.g. needing things like PGP and webs of trust, is the main road-block to secure communication.

    Is there any effort to an "Email 2.0"? I don't know of any projects that aim to be replacement to current email protocols, but maybe they're just badly publicized?