External emails will not forward(Exch 5.5)

[NimrodMCSE]

I'm trying to setup my boss to recieve emails at an external (smtp) address while he is traveling. I did the usual, made a custom recipient with the external address and then went into his account and under deliver options selected alternate recipent and selected the custom recipient I just made. Also selected deliver messages to both. When i send an email to his account from my exchange account he gets the message at both his exchange and external(smtp)accounts. But when I send a message from my hotmail account only his exchange account gets the message, not the external mail account. Don't get any NDRs either. Yes, I do have all the open relay protection setup, but there has to be another way to forward mail externally without disabling that protection.
Thanks,
Nim

 

[zoeythecat]

There is another way to do this. You can do this on his outlook client and create a rule. When you create the rule it will ask if you want to create the rule on the "Client" or the "server". Choose "Server". First, from his outlook client, create a new contact with his external email, then from his outlook client, you go into Tools==>Rules Wizard==>click "new"==>in top windows "check messages when they arrive" and click "next"==>in top window checkmark "where my name is in the to box" and click "next". On the next screen from the top window checkmark "forward it to people or distribution list" and on the bottom window click on "people or distribution list". This will bring up the GAL. Click on the down arrow so you can select "Contacts". Then select the contact you created for your bosses external email. then click "ok". You will now see in the top window and bottom window that any mail coming to his inbox will be forwarded to his external email. (He will get the email in both places. His Exchange Inbox and his external email). Click on "Finish" and you will now have the rule setup.

 

[Guest_imported]

Go to Site Addressing, Routing tab. See if you have more than one entry for SMTP. If so, follow the path to that server and see if the message is in a queue of an MTA. If you have another IMS somewhere, even if it is not being used, if the MTA sees another route other than the local route that the message came in from, it will try to route it out the other way (by design).