Re: Use of the IV in DES & stuffing the first block w/ random stuff

["Josh M. Osborne" <stripes@va.pubnix.com>]

In message <199508152039.NAA15590@ix7.ix.netcom.com>, Bill Stewart writes:
>At 09:52 AM 8/15/95 -0400, you wrote:
>>I have recently started writing a small pair of encription and
>>decription programs.  I was planning of gennerating the key by
>>taking the MD5 of the text password supplied by the user.
>
>A reasonable approach, but be careful in your implementation.
>I haven't seen the book "A Million Wimpy Passwords and their MD5s" yet,
>but the CD-ROM version may be out soon :-)  And you can probably
>ftp it from dockmaster.

I don't know what can be done here other then encuraging the user
to use a long password.

[...]
>IVs are designed to let you put random stuff in them to discourage
>known-plaintext attacks, replay attacks, etc.   However, suppose you
>take a known 64 bits from MD5(password) and put them in the IV -
>instead of the Bad Guy needing to brute-force 168-bit-deep Triple DES,
>he gets to brute force MD5s of human-selected passwords instead,
>which makes a lot of pre-computation possible.

Don't I need to know what goes into the IV?  I can't just stick
random stuff in it - I need to stick something that is a function
of the passphrase into it (or make the user remember something
my program spits out).

>Also, for 3-Key Triple-DES, how do you get 168 bits of key from
>128bits of MD5?  (for 2-Key 3-DES, you only need 112 bits...)
>If you do something like M1=MD5(Key), M2=MD5(M1,Key), realize 
>you've got at most 128 bits of real key instead of 168, 
>though that probably needn't worry you too much...

Oh, I was going to do a MD5 of half of the passphrase to get one
key pair, then MD5 the other half to get another key, and that
left about 64 bits to play with....

[...]
>>Or am I better off putting the extra 64 bits of "key" into the IV,
>>and generating a strong random number to stuff in the first block
>>- since the decoder can just ignore that block anyway.
>Put the strong random number in the IV, if you've _got_ a source
>of strong random numbers...

Don't I need to reproduce the same IV during the decryption?

>You might want to do something fancy like choose a random salt,
>use the salt for the IV, and use MD5(salt,human-selected-key) for the key.
>This makes pre-computation much less useful (unless you're careless
>and use MD5(key,salt) instead if MD5(salt,key)...), and means that
>you use a different session key for each batch of stuff you encrypt,
>even though you're using the same key.  If you're paranoid about replay
>attacks, you could let some of the bits of the salt be random and some 
>be a counter, and never accept a key smaller than the one from the
>previous successfully-decrypted message.

Hmmmm, so I should put the salt in the clear at the start of the file?
This looks like an intresting idea.

(it occurs to me that I never mentioned what my "sample application"
was - I was thinking of encryption backup tapes so they can safely
be transported off site and stored.)