>Your two approaches are to avoid the use of SMTP for transporting these
>messages (i.e. give all administrators a local account, and ask them to
>check their their mailboxes with POP or IMAP; which does not necessarily
>avoid content scanning, but does it in a way that doesn't involve *your*
>reputation); or to evade content analysis by encrypting admin messages,
>either with per-recipient solutions like OpenPGP or S/MIME, or with a
>general shared secret scheme.
>
>Looking at client support, I'd say that OpenPGP is probably the better
>option.

I'd say the opposite.  Every desktop MUA supports POP and IMAP, and
the three major webmail systems, Gmail, Hotmail, and Yahoo, all let
you consolidate your mail by POP or IMAP from other accounts.  None
of the webmail systems support PGP or S/MIME except maybe by some
experimental add-ons.

What I've done for some of my users who want their mail forwarded to a
gmail address is to run it through spamassassin.  If the spam score is
low, I just forward it so they get it right away.  If the score is
high I drop it in a local mailbox so they get it eventually when gmail
picks it up by POP.  Works pretty well.

R's,
John

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