I've been asked the feasibility of doing something similar.  

There are also commercial products which work by snooping the
network traffic.

Previous replies in this thread have suggested using add_recipient() and
resend_message().  However, neither of these methods will preserve the
actual recipients.  That doesn't seem to meet the intent of a wiretap
effort.

Presumably, the results of the wiretap will need to be something that is
easily searchable by someone in a legal department or security department.
They'll probably want to use off-the-shelf tools that were designed for
scanning a live Exchange or Notes server.  It seems to me that you need
to create new headers to show what was in the envelope.  I'm thinking that
a wiretap on a transit server needs to send the copies to some back-end
mailbox system where searches and analyses can be run.  This doubles the
amount of outbound e-mail. You don't want to re-check for viruses or spam.
You might need separate queues or a separate configuration for the wire-tap
queue.  Of course, the back-end system may go down or get bogged down.

I envision a design where a separate sendmail listener is used to receive
the wiretap copies.  (But that's mostly because I'm currently doing virus
scanning with commercial milter.)  I see "repairing" the from, to, and cc
headers to reflect what is really in the envelope and adding x-wiretap-xxx
headers to record what the original from, to, and cc headers were.  I'm
looking at using Net::SMTP for the wiretap.  Using the datasend() method,
it's easy to send the real, munged, or created headers.  The body can be
sent with $entity->stringify().  I suspect that stringify() is a bit
expensive, though.  It would be nice to use some sort of connection caching
on the SMTP connections to the wiretap, but I don't know if that's possible.

At any rate, it seems somewhat expensive to do a wiretap properly and anyone
requesting one should be asked to provide the additional mailserver resources.

Comments or flames on this design?


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