Uli and all,

I've found the problem, I hope my solution will help in the future.

If you want to send signed & encrypted email to outlook or messenger, you have
to sign THEN encrypt the all message.
As far as I've seen encrypting THEN signing isn't a good solution since in that
case two icons appears in messenger, one "signed" and one "encrypted". So one
icon says that your email was encrypted but not signed, and the other one says
it was signed but not encrypted... Very strange.

The problem was that at the end of the input I gave to the smime -sign utility,
there were two LF. If only one LF is at the end of my MIME encoded content, the
email is all well in outlook and messenger.
A valid file (with attached file) you could give to the smime -sign utility is :

<snip>
Content-Type: multipart/mixed;
    boundary="XXXXXXXXX.506.481.970048768.734.506"

Il s'agit d'un message multivolet au format MIME.
--XXXXXXXXX.506.481.970048768.734.506
Content-type: text/plain
Content-Transfer-Encoding: 7bit

Body

--XXXXXXXXX.506.481.970048768.734.506
Content-Type: text/plain; name="attach"
Content-Transfer-Encoding: 7bit
Content-Disposition: attachment; filename="attach"

Attach

--XXXXXXXXX.506.481.970048768.734.506--
</snip>
ONLY ONE LF HERE.

I think that, once the email is decrypted, outlook change "on the fly" the
signed part because he doesn't like the way the "boundary" appears, so the
signed part isn't valid anymore. Messenger doesn't have to change the signed
part so it's still valid.

Sorry for the poor english.


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