cat /dev/DiBona/brain: What About E-mail Security?

Let's start with TLS while we wait for SPF.
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Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

The ONLY WAY to ensure completely secure email is to use either Gnupg or PGP. The message retains its encryption and security from sender to receiver... Just how many mail servers the message transits thru is irrelevant.

Further more, key generation and distribution are under the complete control of the individuals concerned.....

Peterson...

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

Or, use an S/MIME certificate. S/MIME has a greater chance of being widely accepted because the most popular (not necessarily the best) mail clients support it. S/MIME is probably easier to use for the average user. That said, I even got Mutt to sign/verify and encrypt/decrypt using the certificate/key (PKCS12 file) I exported from Mozilla, took apart with openssl, and whose components (cert, key, intermediate CA, and root CA) I put in the files Mutt expected them to be in. Admittedly, I find myself hitting (S)/MIME-(f)orget_it before sending in most cases because most people use S/MIME certs as much as they use PGP/GPG -- which is hardly ever.

Disclaimer: I work for a CA and use my S/MIME cert as much as possible -- even for client authentication to our company website. Later versions of curl can even use S/MIME certs to authenticate itself to a website that requires client authentication.

the crypto specified in the

Anonymous's picture

the crypto specified in the S/MIME standard is too weak to provide reliable security, it's only protection against casual snoopage

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

Or tell everybody to get a free personal certificate from Thawte or use PGP. Then you don't have to change anything on the server.

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

Thawte certs are the best :)

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

The biggest problem with implementing TLS mail is all the poorly configured TLS mail servers presently online that break mail sending when trying to negotiate TLS with each other. This is the biggest barrier to widespread TLS use

Stephen
meridian@tha.net

Secure telnet since 1993 at the latest

amarsh04's picture

Secure forms of telnet have been in existence since 1993 or earlier, and there are implementations that support authentication and encryption.
http://www.columbia.edu/kermit/telnet80.html is a good place to start learning more about security options in telnet.

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

What advantage does this offer over generating your own cert with openssl?

I don't see FreeSSL.com in any of the lists of trusted CAs I quickly checked, so I'm not too sure how they can beat 'mydomain.com.au' the new self-signed CA.

Their https server uses a cert signed by usertrust.com, which is in turn self-signed. If the same is true of their certs for sale, I may as well just generate my own instead.

We already use our own root CA to generate client certificates (which we require to grant access over the 'net) for users who want remote HTTPs, SMTP and IMAP access. We also make server certs for TLS-protected LDAP, HTTPs for use on the intranet. I'm very surprised this option wasn't mentioned in the article. Perhaps I've missed something.

--
Craig Ringer

Re: cat /dev/DiBona/brain: What About E-mail Security?

Anonymous's picture

Also, you can get free (as in beer) certificates from cacert.

Re: POP and IMAP

Anonymous's picture

Except that S/POP and IMAP/S are pretty well-known and many clients have GUI interfaces that allow the user to simply "Click here to autoconfigure" and they figure out if your server supports secure versions of POP and/or IMAP and then uses them, if available.

Of course, none of this protects your mail while it sits in the spool area of the various mailservers that it transits through. Which is why PGP/GPG encryption is truly the only way to secure email, since it's fully endpoint-to-endpoint encryption. It doesn't sit plaintext in some mailserver's spool directory...

Re: POP and IMAP

Anonymous's picture

Which is why PGP/GPG encryption is truly the only way to secure email

Mmmm... I don't agree. What about S/MIME?

S/MIME doesn't offer the

Anonymous's picture

S/MIME doesn't offer the choices nor the security of properly configured PGP or GnuPG. S/MIME is a distant second choice that needs to be updated to offer strong crypto and appropriate pubkey lengths or it's only protection against casual snoopage. The guy who said PGP/GPG is the "one true way" is correct.

pop/imap

Anonymous's picture

no mention of encrypting pop/imap huh? You've only taken care of outgoing mail and completely ignored incoming mail in which your password is typically sent in the clear.

Re: pop/imap

Gamara's picture

I wanted to keep the article focused and to the point, as the other commented noted, many people have and use pop-s and imap-ssl, but in my experience tls enabled servers aren't as common as I'd like them to be....hence the articles focus.

That said, please, everyone, use pop-s or imap-s :-)

Chris DiBona

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