RE: [Full-disclosure] S/Mime Exchange 2003 how secure how to secure it?

[Lyal Collins]

Title: Message

Do you want data recovery? Just forget the password to a certificate/private key, and the company has lost access to any comany records 'protected' by S/MIME, generally in conventional S/MIME setups.  And forget virus/spam scanning too.   Lyal         -----Original Message----- From: [EMAIL PROTECTED] [mailto:[EMAIL PROTECTED] On Behalf Of Daniel Sichel Sent: Wednesday, 29 March 2006 3:54 AM To: full-disclosure@lists.grok.org.uk Subject: [Full-disclosure] S/Mime Exchange 2003 how secure how to secure it? Directive has just come down from on high, we WILL use email on our Cell Phones/PDAs and non VPN’d laptops.  I am not a messaging guy but at a small telco you wear lots of hats so I could use some real help here. We are upgrading shortly to Exchange 2003 on Windows Server  2003 and want secure email to and from our cell phones etc. So here are my questions   How secure is the built in S/Mime in Exchange 2003 assuming we are using a certificate  for session encryption ? Don’t laugh and hoot, I am looking for real data not speculation. Are there exploits, and if so what is needed to carry them out, physical access, just need the phone number, or what?  Can this be brute forced?   I would like two factor authentication using the users password and something inherently in the cell phone like a burned in serial number or the DN or something. Is there any support  for such a thing that will work on cell phones and/or PDAs ?   I know OWA sucks on Exchange 5.5 and 2000, how about 2003? Same questions as above, is it exploitable, and if so how? Can we require a machine accessing the OWA site to flush its cache when done? Hopefully this can be forced without requiring an OK click, I just want to do it, no user intervention required (or allowed).   Any help would be welcomed, any Microsoft bashing would be a waste of time since the higher powers have spoken and you know how that goes, So it is written, so shall it be done.   Thanks     Daniel Sichel, MCSE, CCNP Network Engineer Ponderosa Telephone

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