On Exchange Server 2010, is there a way to monitor the number of external recipiants on an email with attachments?
The Problem: From time to time, we have a couple of users who will send out 3 and 5 meg files as newsletters to several hundred clients. This brings our outgoing bandwidth (Bonded T1) to its knees. We've tried teaching delayed delivery with no affect on behavior. What we'd like to do is monitor outgoing mail for all email greater than 'X' of external recipients AND an attachment.
Complications: We need to allow for up to 15 meg files as a matter of business. We need to allow for 100+ external recipients also. We only want to know when both criteria are met so we can bring down the pain!
Is there a way to do this in Exchange natively? Are there third party products available?