CF9 Web Server relay to Exchange 2010

So where did the emails go before the fix?  Is there a way to recover those that went into limbo?

Problem has been resolved.

Short answer:

"Externally Secured Authenication" is a required setting under Authentication. Anonymous Users selected on Permission  Group IS NOT enough.

Detail Answer:

Under Exchange 2010 EMC, goto Server  Configuration > Hub Transport. Create a new Receiver Connector. Add  the IP address of your Coldfusion server or just except everything in  your subnet by adding /24.  Under Authenication select ONLY "Externally  Secured (for example, with IPsec)" <--- IMPORTANT deselecting  everything else. Dont worry if you forget that as it will not let you  select any other combination. Under Permission Group select everything  (may not be required, but I know it works that way).  Click OK and you  should be good to go.

Some notes:

First and foremost, the paramater debug for cfmail writes all of the information needed to troubleshoot this issue into the log file \runtime\logs\coldfusion-out.  Second, do not rely on the "verify server" option. Maybe the only thing that does is checks if the server is pingable but it does not actually send message or anything that is particularly useful. Adobe, please take a page out of other programs rule book and actual do something with this feature to make it worth while (ex: Server Alert software I use for monitoring system temps, sends an actual message and displays the complete event below the test connection button).

Next, like above, do not rely on the regular logs as "message was successfully sent" means nothing, with the debug logs say otherwise.

When the actual message is blocked by Exchange due to a relay issue, and the actual debug logs shows this information, how is the message sent success? That gives false hopes and send people on a wild goose chase!

Mine you the issue was Exchange, but the feature to verify server and normal mail logs should provide actual details instead of assuming.

If it helps in, I created a CFM file using cfmail pointing to both the old server and the new server. Emails go out fine until I add an external email address (ex: @gmail.com). From there no messages are sent nor received by Exchange. If I remove the external address, the email is sent and received by Exchange and therefore accessible on the client.   Emails are able to be sent externally from any other client (Outlook 2007/2010).  It is as if CFMAIL does not seem to want or understand how to handle external addresses with Exchange 2010.

Hi Jeff,

I usually find helpful connecting from the CF server to the exchange server and keying in the SMTP commands. Sometimes you get an error eg Relay deny or such and can then debug the exchange connector rules. EG:

From CF server telnet (or PUTTY some other telnet tool) exchange 25

220 domain Microsoft ESMTP MAIL Service, Version: 7.5.7600.16544 ready at  Wed, 9 Mar 2011 10:52:10 +1000
helo
250 domain Hello [127.0.0.1]
mail from:sender@domain
250 2.1.0 sender@domain....Sender OK
rcpt to:recipient@domain
250 2.1.5 recipient@domain
data
354 Start mail input; end with <CRLF>.<CRLF>
subject:test mail
message text
.
250 2.6.0 <gACiXeRbD00000001@domain> Queued mail for delivery

HTH, Carl.