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03.19.2008 at 04:28AM PDT, ID: 23253159
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9.3

Windows Server 2008 cannot connect via SMTP to certain external mail servers incuding hotmail.com

Asked by mkraftman in Simple Mail Transfer Protocol (SMTP), Exchange Email Server, Windows 2003 Server

Tags: , ,

The problem originally manifested itself in mail not being sent out from Exchange through a Send Connector to certain domains only including hotmail.com. Messages just sit in the queue. Logs indicated repeated attempts to open the SMTP connection fail.
I then followed the procedure in the TechNet article "How to Use Telnet to Test SMTP Communication" http://technet.microsoft.com/en-us/library/bb123686.aspx. Those domains to which mail cannot be sent behave strangely in telnet. When you open a connection on port 25 nothing happens until you type a few keys, then you get the 220 response. For domains to which mail can be sent fine you get the 220 response back straight away.
There are two Windows 2003/Echnage servers on the same netword that don't experience the problem.
I have used the telnet technique on these and you get the expected immediate 220 reponse from all domains including the problem ones.
it seems that there is some problem with the WIndows Server 2008 TCP stack.Start Free Trial
[+][-]03.19.2008 at 07:44PM PDT, ID: 21167865

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About this solution

Zones: Simple Mail Transfer Protocol (SMTP), Exchange Email Server, Windows 2003 Server
Tags: Microsoft, Windows Server 2008 with Exchange Server 2007, Windows Server 2008 Standard x64 RTM; Exchange Server 2007 SP1
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Solution Provided By: Netman66
Participating Experts: 1
Solution Grade: A
 
 
 
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