So this is what I am very close to having in good working shape:

For each email message processed by the courier server, I collect the
recipient addresses from those messages that come from an authenticated
user (Using the Courier::Filter::Message::trusted() property). I store
these addresses in a DBM file.

Then for each mail message that comes from an unauthenticated user
(generally speaking, regular inbound smtp traffic), I grab the sender
information (Courier::Filter::Message::sender() property). I can then
check this sender information against my DBM file, and determine if this
sender is someone who was sent a message from an authenticated user on
my server.

The problem, of course, is that the 'sender' information, which is taken
from the MAIL FROM: smtp command, is easily and often faked.

My original, and flawed thinking, was to allow messages who's sender was
in the DBM file to bypass the normal spam filters.

So my questions are:

1. Is using the 'sender' property to potentially bypass the spam filters
and let the message be delivered to the INBOX going to prove useful at
all? Or are the chances of the forged 'sender' address being the same as
one of the addresses in my auto-whitelist DBM file too high? 

What if I categorized the recipient addresses by sender (user jason has
sent messages to '[EMAIL PROTECTED], [EMAIL PROTECTED], [EMAIL PROTECTED]'), then when 
checking user
jason's inbound smtp traffic, check the sender information only for
those addresses that he has sent messages to previously?

2. What if I combined this filter (Is the sender in my known recipeients
DBM file?) with an SPF check such that the 'sender' info is only trusted
for messages who pass an SPF check?

3. Are there other, more clever ways to use this DBM file of trusted
recipient addresses in a way that would help me (and my spam filters
like spamassassin, DSPAM, and CRM) better classify spam vs. not-spam?

Suggestions welcome. Once I get the final version ready, I'll post a
cookbook on how I put it all together.

Thanks,
jason



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