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I have read numerous articles and done everything recommended to setup a mail server in windows 2008R2

I am simply trying to send messages from my server from certain websites that I host.

I queued mail for delivery then got this back....

4.4.7 Unable to deliver message to the following recipients, due to being unable to connect successfully to the destination mail server.

For reference, I followed the instructions here... How to setup an SMTP server Is there something I am missing?

Judson Terrell
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While I am not familiar with Windows mail servers, I have encountered a similar issue. If this only happens with some destinations, the receiving mail server could be simply refusing the connection.

For example, mail servers often refuse connections from IP addresses that ISPs hand out to "regular" (non-business) customers. Another common reason to reject mail is if the reverse DNS entry for your IP doesn't match the hostname in the HELO (or EHLO) command. (However, in that case, you probably wouldn't get "unable to connect" errors.)

You could try online tools like mxtoolbox to help diagnose the problem.

Daniel Koszta
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