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Re: Web Tool Announcement: ismymailsecure.com
From: Brian Behlendorf <brian () behlendorf com>
Date: Wed, 25 Aug 2010 16:56:48 -0400 (EDT)

On Wed, 25 Aug 2010, Tim wrote:
It's unfortunate that STARTTLS is currently a disaster to configure
securely, particularly because it is just a point-to-point encryption
mechanism and all of this complexity has to be addressed at every hop.
I think as a security community we'd be a lot better off putting our
efforts into encouraging end-to-end encryption with S/MIME or
PGP/MIME.

That's the conclusion we came to in the NHIN Direct project (http://nhindirect.org/, secure messaging for the health IT industry) though server-server TLS with agreed-upon CAs (establishing "trust circles") are helpful. What TLS didn't appear to allow is negotiation of CAs - which ones do I trust, which ones do you have signatures from, what's the intersection. That would allow it to grow more intelligently than the "trust this long list of root CAs" model that web browsers use. In our case it's useful to also encrypt the server-server link, even if you are S/MIME encrypting the message content, because From/To/Subject data can be pretty sensitive. Seeing encrypted SSL traffic between suttermentalhealth.com and healthvault.com is a lot less revealing than From: drbob () suttermentalhealth com To: brian () healthvault com Subject: Are you taking your meds?

        Brian


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