Setting rules for outgoing e-mail

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Is there a way to set rules for outgoing e-mail? For example, any mail sent from user1@mydomain.com to an outside user should automatically get copied to user1's boss, user2@mydomain.com.
This can get very complicated, depending on what you want to do. There are several products out there that perform this function, especially to comply with NASD rules for supervision. Legato has a product for this that works very well. As for a rule, you could try writing some script, but it could get messy and bog down your router. Server-based rules are really only for incoming messages, not outgoing ones.

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Reverse DNS attacks and tarpitting I have an email server that has been running flawlessly for two years. Recently, I have been seeing an increase in the number of messages seemingly "stuck" in the SMTP queues... They seem to be replies from postmaster@mydomain.com to spam sent to nonexistent users in our domain... This is causing mail to back up and I have to go in manually and delete the offending messages from the SMTP queue... Any ideas on how to stop this from happening?

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