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. ______________________________________________________________________ OpenSSL Project http://www.openssl.org User Support Mailing List [EMAIL PROTECTED] Automated List Manager [EMAIL PROTECTED]