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How to Check email communication between two servers

Hi Guys, what is the best way to check email communication between two servers.

Scenario:  we have an MS Exchange 2007 and sending out email using a smart host.
                  There are two companies claiming they are not receiving email from our end.
                  besides those two everyone else are okay.
                  Tested sending to a one address and really never got there but never got a
                  non delivery message. check queue viewer didn't find any stuck jobs.

is there a test that I can run to will conclude message went to their server?
how do I do it?
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Bill Bach
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