Searching mail that arrived encrypted on Outlook Server

Eliot, Christopher christopher.eliot at
Tue Jul 22 20:59:40 CEST 2008

We use a typical Microsoft Outlook server setup.  We use GPG to encrypt
mail coming and going over those internet tube things.

My problem is that I'd like to be able to use the Outlook search
facility to search through old mail that I've received or sent.  Right
now it appears that any mail that arrives or that I send is stored in
encrypted form on the Outlook server, and that the search mechanisms
just search the encrypted text, not a decrypted version of it.  Which
makes searching unusable.

I consider our Outlook server sufficiently secure for my needs here; I
don't feel that I need to encrypt each email there.  So I'd like my
email items to be stored unencrypted, so that I can do searches on their
Alternatively, if the search mechanism could somehow be taught to
decrypt mail before searching it that could work, but I imagine it would
be very slow.

Right now I can sort of achieve what I want by forwarding arriving email
to myself with encryption disabled, and saving the result.  This of
course is tedious, and also means that the email is listed as being from
me, rather than from whomever really sent it.

Does anyone have a better suggestion for this?

Topher Eliot
christopher.eliot at
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