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SMTP Traffic Monitor

I'm looking for suggestions on a tool that can monitor SMTP traffic.  I've used a few monitors that can ping each appliance and give me up/down alerts, but I need something that can authenticate to our system and verify delivery of a test message.  The problem is that we have a fragile email filter that is technically "up" according to all monitors, but for various reasons will stop passing traffic, and will just queue all messages.  Any suggestions would be appreciated.  If anyone knows of a free tool that can do this, that would be preferred, but I'm interested in anyone's opinion on any tools they have used and had a good experience with.  

Our environment:
-McAffee Secure Mail  6.7.1 (the filter that is causing problems)
-Exchange 2007 and 2003 mixed environment (has been rock solid, but messages can't get to Exchange if Secure Mail stops passing traffic)
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peakpeak
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Thanks for the comment.  We are currently able to track messages in our environment.  What we need is a live monitor (something more in depth than just a ping) that can tell us if messages are not successfully being delivered.  
Thanks.
That is the Purpose of Message Tracking ....
I'm sorry, maybe I wasn't clear enough.  By live monitor, I mean something that can alert us (email or text message) in real time if messages are not being deliverred.  We're looking for a hosted service, or at least running on a machine outside of our environment, because it would need to be able to send us a message in the event of our environment being down.  I've been using mon.itor.us, but it doesn't catch a failure if the traffic gets stopped within our organization.  It only catches a failure if the server is completely unresponsive.  In our case, the server is still responding to pings, but is queueing messages, and not allowing any traffic through.  Events like that have happenned recently, and we're looking for a monitor that can catch that outage as soon as it happens.
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grv
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Correct URL for second hosted service is actually www.mailive.com.