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> [-] Fixed a bug of Beta/2 with S/MIME internal implementation. It didn't
> check correctly the signatures.

> If I change the S/MIME engine to 'Microsoft CryptoAPI' all signed mails
> are checked correctly.

Be careful - CAPI may be checking the signatures incorrectly
there - they might be bad (damaged in transit, perhaps?
Malformed?).

There's a known critical bug in MS CryptoAPI, which affects IE's
SSL, Outlook (and OE's) S/MIME, and presumably The Bat!'s S/MIME
if you choose to use that too - as well, I suppose, as
Authenticode for automatic updates and ActiveX controls, but
no-one's exploited either of those - yet. (OpenSSL had a similar
bug - it was fixed more or less as soon as they were reported
vulnerable.)

CAPI doesn't check the basic restraints on certification keys,
and will mistakenly verify as correct a signature where a
normal, CA-certified server (or mail) key acts (outside of its
constraints) as an intermediary CA. So, for example:

[Issuer:VeriSign | Subject:VeriSign]
- -[Issuer:VeriSign | Subject:[EMAIL PROTECTED]]
- --[Issuer:[EMAIL PROTECTED] | Subject:Bill [EMAIL PROTECTED]]

...shows up as a valid signature chain. (You have to actually
check the certificate chain very carefully on every message/SSL
exchange to see the difference.)

Yes, this allows practical man-in-the-middle attacks on SSL, and
it breaks S/MIME too.

I haven't actually tested whether The Bat! is vulnerable if
using MS's CryptoAPI. I could probably do that if you like, but
I'd guess it probably is.

I also wouldn't be shocked if The Bat! uses OpenSSL for its
implementation, and if the upgrade to that library ... in fact,
yes, it does (checked with a hex editor and OpenSSL strings are
clearly visible in 1.61). Assuming TB checks the basic
constraints, it'll be okay. (In fact, that might be the bug
talked about at the top of this message, that was fixed.)

So, I'd avoid CryptoAPI for the time being, if I were you, I'd
stick with TB's implementation...assuming you can get it to work
of course.

MS aren't taking the problem even remotely seriously, by the
way, which is attracting a lot of fire on Bugtraq. Don't expect
a fix until MS have stopped throwing a tantrum and the politics
have died down.

- --
/sjx.

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