Source: Microsoft Support

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Mail between RGs is slow to non existent and sometimes the queues go into retry states.

Mail flow can be affected both ways and sometimes only one way RGs are connected via VPNs.

Telnet to server that is in retry state and ehlo returns:

220 servername Microsoft ESMTP MAIL Service, Version: 5.0.2195.6713 ready at  Tue, 
20 Dec 2005 14:34:09 -0800 
ehlo 
250-Computer.domain.com Hello [192.168.1.34] 
250-XXXA 
250-XXXB 
250-SIZE 
250-ETRN 
250-PIPELINING 
250-DSN 
250-ENHANCEDSTATUSCODES 
250-8bitmime 
250-BINARYMIME 
250-XXXXXXXC 
250-XXXD 
250-XXXXXXXXXXXXXXXXXXXXXXXE 
250-XXXXXXXXXXXF 
250-AUTH GSSAPI NTLM LOGIN 
250-XXXXXXXXXG 
250-XXXXXXXXXXXH 
250-XXXXXXI 
250 XJ

Netmon caps show OD OA in packet but not the completition of a second OD OA to signify the completion of the message. We never see the Fin sent or received. There is a 625+ second delay before we time the connection out.

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CISCO Router filtering and then dropping what it deems as 'invalid SMTP command' packets. See resolution below for more information

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Contacting CISCO to check configuration of the Firewall for SMTP
CISCO removing firewall feature set for testing
CISCO says it was logging an invalid SMTP command
ESMTP verbs cleaned up now
All mail dequed

The CISCO Feature set provides "Firewall like" features to inspect packets and prevent "abnormal" packets from being transmitted. The feature set does a stateful inspection of the packets looking for the abnormal packets and block these. In the log it was showing an invalid SMTP command

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