[ Caution Outlook ] Quick question on MS Outlook and PGP

[warlord at MIT.EDU (Derek Atkins)]

Matt Brodeur <mbrodeur at NextTime.com> writes:

> On Thu, Mar 15, 2007 at 09:26:28AM -0400, Ted Roche wrote:
>>
>> MerriLUG this very night. He practiced this presentation at CentraLUG
>> recently and did show a little bit about Outlook, although the demo
>> gods were not kind to him that night. You might want to try to make
>
> That particular part of the demo was a direct result of my failure to
> read the directions.  From http://www.g10code.de/p-gpgol.html:
>   Here is a major problems we are aware of (2006-04-12):
>     * It does not work with versions of Outlook older than OL2003SP2. 
>     * The version check which warns about too old Outlook versions does
>       not work reliable.
>
> I'll actually have that demo working tonight, really.  This time I
> have Outlook 2003SP2 and the latest and greatest GPG tools from
> http://www.gpg4win.org/.  It'll have to be something different that
> breaks this time.

My understanding is that recent versions of Exchange (it's not
Outlook, per se), don't store messages in RFC822/MIME format, but
internally shred the documents into different parts.  So when it has
to output a MIME message it needs to rebuild it on the fly.
Apparently it doesn't understand the multipart/encrypted that PGP
Encryption uses and so it creates a multipart/mixed message,
which is violating all the various specs.

Some co-workers of mine are still looking into this issue.

-derek

-- 
       Derek Atkins, SB '93 MIT EE, SM '95 MIT Media Laboratory
       Member, MIT Student Information Processing Board  (SIPB)
       URL: http://web.mit.edu/warlord/    PP-ASEL-IA     N1NWH
       warlord at MIT.EDU                        PGP key available

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