The error message in the "Symptoms" section of this article is closely related to the following Exchange Server generated error
message:
550 Relaying is prohibited
The message route of this topology is:
Sending Exchange Server ----- Internet ------ Firewall ----- Mailhost
The SMTP conversation of this problem may look like the following log:
A connection to 10.1.1.25 was established.
<<< IO: |220 firewall.expedia.com Generic SMTP handler
<<< 220 firewall.expedia.com Generic SMTP handler
>>> EHLO ExchangeSending.microsoft.com
<<< IO: |500 Command unrecognized
<<< 500 Command unrecognized
>>> HELO ExchangeSending.microsoft.com
<<< IO: |250 firewall.expedia.com talking to
mailhost.expedia.com [157.5.1.4])
<<< 250 firewall.expedia.com talking to mailhost.expedia.com ([157.5.1.4])
>>> MAIL FROM: <bob@microsoft.com>
<<< IO: |250 <bob@microsoft.com>: Sender Ok
<<< 250 <bob@microsoft.com>: Sender Ok
>>> RCPT TO:<vincent@expedia.com>
<<< IO: |550 Domain invalid
<<< 550 Domain invalid
>>> QUIT
<<< IO: |221 firewall.microsoft.com closing connection. Goodbye!