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From: "Arnold G. Reinhold" <[EMAIL PROTECTED]>
Subject: [Mac_crypto] Apple should use SHA! (or stronger) to authenticate
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Date: Sun, 4 Apr 2004 06:17:55 -0500

The cryptographic hash function MD5 has long been used to
authenticate software packages, particularly in the Linux/Unix/open
source community. This has carried over to Apple's OS-X. The MD5 hash
of an entire package is calculated and its value is transmitted
separately from the package. Users who download the package compute
the hash of the copy they received and match that value against the

Putting aside the question of how the the hash value is safely
transmitted, there is a potential attack on this method due to the
128 bit length of the MD5 hash output. If all the individuals having
input to the creation of the original software package are
trustworthy, then 128 bits provides adequate security. Someone trying
to substitute a version of that package containing a malicious
modification (Trojan horse, virus,  backdoor) would have to solve a
128 bit problem to create an infected package that passed the hash
verification. That is considered computationally infeasible, at least
until the advent of quantum computing.

One might think the above argument proves MD5 is sufficient. After
all, if an attacker had an agent working inside the organization that
produced the package, that agent could simply incorporate the
malicious software patch in the original package. However such an
insertion is very risky. A sophisticated software company would
likely have code reviews that would make introduction of the
malicious code difficult. Use of a source control system makes is
easy to track down whoever inserted the malicious change once it is
discovered. The malicious code would be distributed to everyone,
increasing the likelihood of detection. In an open source model, a
defect in source code is particularly hard to hide. The agent risks
being uncovered and and perhaps prosecuted, the organization he works
for risks being identified and the technical means that the malicious
code employed would be compromised.

A safer attack would be for the agent to insert an apparently
innocent modification to the package, with the modification selected
so that the MD5 hash of the package with the malicious code matches
the hash of the officially released package. Since the attacker (or
whomever he is working for) controls the malicious code, calculating
the value of this modification is subject to a meet-in-the-middle
attack and presents presents a 64-bit problem. Solving such a problem
is within the means of a well-funded attacker today* and will become
easier in the future.

The modification could be designed to get past code reviews in a
number of ways. For example, 64 low order bits in a JPEG icon might
be altered. The agent would have to make the last modification to the
software package prior to release and perhaps send a final
pre-release version of the package to someone on the outside who does
the collision calculation, but those are hardly insurmountable
hurdles.  In situations where new releases are relatively frequent,
it may suffice for this attack to succeed only occasionally, allowing
periodic entry into selected systems to recover private keys, for
example.  The attacker merely submits modifications late in the
release cycle and if his happens to be last then the full attack is

The obvious solution to this problem is to use a wider hash for
package authentication. For example, SHA-256 would present an
attacker using this approach with a 128-bit problem. Even SHA1 would
be preferable, making such an attack an 80 bit problem.  If both MD5
and SHA1 hashes are provided, the attacker faces the problem of
forging them both. It costs almost nothing to provide a wider hash
along with the MD5 hash whenever a new package is released. It seems
the prudent thing for Apple to do.

Arnold Reinhold

* From: http://www.rsasecurity.com/rsalabs/faq/3-6-6.html

"Van Oorschot and Wiener [VW94] have considered a brute-force search
for collisions (see Question 2.1.6) in hash functions, and they
estimate a collision search machine designed specifically for MD5
(costing $10 million in 1994) could find a collision for MD5 in 24
days on average. The general techniques can be applied to other hash

P. van Oorschot and M. Wiener, Parallel collision search with
application to hash functions and discrete logarithms, Proceedings of
2nd ACM Conference on Computer and Communication Security(1994).

** SHA1 is available in OS-X as part of openssl. Type "openssl  sha1 filename"
mac_crypto mailing list

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R. A. Hettinga <mailto: [EMAIL PROTECTED]>
The Internet Bearer Underwriting Corporation <http://www.ibuc.com/>
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