I'm running into an occasional issue where SMTP routing seems to be going awry. In Exchange 2003 Message tracking, I'm getting a message that "Message transferred to smtp through SMTP", but the message never gets delivered and no NDR is generated. Normally, on a successful send, the message would say: Message transferred to servername through SMTP So ... something seems to be confusing this server into mis-routing some outbound messages within SMTP, essentially treating the lowercase name smtp as its own server. The only additional tidbit that I can add: we typically see this issue when someone is using their cached list of addresses in outlook. When you look in your sent items folder, the recipient will have single-quotes around their name. What's odd about this is when you look in message tracking, the single-quote is nowhere to be found, and the appropriate address appears. Inbound delivery is working normally. Any thoughts or suggestions?

What happens when you restart the SMTP service? Do the messages then bounce back or are delivered?Have you applied the latest hotfix?http://support.microsoft.com/kb/950757/en-us"E-mail senders do not receive an indication that some messages have been held by Exchange Server 2003 until the SMTP service, the Microsoft Exchange Information Store service, or the Exchange server is restarted"

On Sat, 24-Oct-09 06:02:25 GMT, Exchange server 2003 wrote:nal tidbit that I can add: we typically see this issue when someone is using their cached list of addresses in outlook. When you look in your sent items folder, the recipient will have single-quotes around their name. What's odd about this is when you look in message tracking, the single-quote is nowhere to be found, and the appropriate address appears. Inbound delivery is working normally. Any thoughts or suggestions? Message tracking logs tell you only half of the story. Do you see anyattempt to deliver the message in the SMTP protocol logs?---Rich MatheisenMCSE+I, Exchange MVP--- Rich Matheisen MCSE+I, Exchange MVP