Encouraging email security.

Jean-David Beyer jdbeyer@exit109.com
Sun May 18 03:30:02 2003


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Daniel Carrera wrote:
 > I was thinking about how most people have no understanding or
 > interest in email security.  OpenPGP is hard enough to understand and
 > use that getting the majority of the population to use it seems a
 > formidable task.
 >
 > I thought of a compromise that might be a step forward.  I was hoping
 > that those who know more about this than I could offer an opinion.
 >
 > There could be a mail client with the following properties:
 >
 > 1) Automatically creates a pre-defined key setup (e.g. 4096 RSA, 1024
 > DSA, 2048 ElGamal). 2) Automatically signs, and encrypts emails (when
 > the pub key is available). 3) Here is the big one: It stores the
 > user's password in the hard disk, in the style of Mozilla, so that
 > the user doesn't have to type it.  It all happens automatically.

Well, Mozilla can do both the VeriSign kind of S/MIME signatures and the
GnuPG kind (with Enigmail, though Enigmail does not work with my 
Mozilla) already. And mutt can do GnuPG signatures just fine. But in 
each case, the user must type in a passphrase. I suppose they would both 
accept a NULL passphrase, so you could just press "Enter" or something, 
but it would sure expose the user to risk. I imagine the programs could 
be setup to notice NULL passphrases and not even prompt for a password. 
N.B.: I am sure not requesting this!
 >
 > This would be a significant down compared to the proper use of
 > OpenPGP, but a significant up compared to what exists today.  Now
 > emails would go around signed and encrypted.

Well, perhaps so, but AOL users and msn.com users seem to get all kinds 
of problems with MIME attachments, which is where the signatures 
normally go. True, you can stick them in inline, but that seems to be 
getting passe'. AOL seems to assume that if there is any MIME, that all 
attachments are of the same type as the first, and this is generally 
false. msn.com users apparently get it that the e-mails are all 
attachments and they see nothing unless they open the various 
attachments. So there will be a lot of resistance to people sending out 
anything in MIME and that includes signatures. I am not sure what AOL 
would do if confronted with an encrypted e-mail: probably bounce it as a 
virus. ;-(

 > In order to read a
 > message an attacker would have to get the password from the
 > recipient's hard drive.  A determined attacker could certainly do
 > that, but the casual one would not.

That is rather difficult with some systems. There is a large software 
manufacturer with a reputation for delivering products that are easy to 
infiltrate, though.
 >
 > Today's email system is about as secure as a postcard. This
 > alternative would raise the bar somewhat bit above sending mail in a
 >  sealed envelope.  It raises the effort needed to eavesdrop in a
 > conversation or impersonate someone.
 >
 > Any thoughts?
 >
It is interesting, but it has taken about 10 years for MIME to not be 
accepted by some large ISPs. I think digital signing and encryption will 
take at least as long, since so few users see any point in it.

I think your analogy is not quite correct. Present e-mail is about as 
secure as a postcard. Signing and encrypting would be more secure than 
using an envelope: it would be using a steel strongbox with a good lock, 
but where the intruder knows where the key is and can break in and get 
it with varying amounts of effort depending on OS, sophistication of the 
user, etc.

The biggest minuses, as far as I am concerned, is that people will get a 
false sense of security when their e-mails are signed and encrypted, but 
their private keys too easily available. When you get a signed and 
encrypted e-mail, you tend to believe you know who sent it and that it 
has not been tampered with or read. But if all someone need do is hijack 
(remotely, even) a machine and get the private key, you are in big 
trouble with identity theft, etc.

-- 
   .~.  Jean-David Beyer           Registered Linux User 85642.
   /V\                             Registered Machine    73926.
  /( )\ Shrewsbury, New Jersey     http://counter.li.org
  ^^-^^ 9:05pm up 2 days, 23:00, 3 users, load average: 2.21, 2.13, 2.10

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