Internal relay not working for Outlook clients
We are trying to move a few users from Exchange 2007 to an external ISP. Following various guides online , we've changed our Accepted Domain to be "internal relay" and created a second "Send connector" for *.company.com to an external smart-host. We then disabled the Mailbox for one Exchange user. The AD user is kept, just the Mailbox disabled (which says it removes mail-enabled attributes from the AD user). The AD user account still has the correct email address in the "email" field on the General tap. Several people in the office are using OS X Mail (Snow Leopard with Exchange integration). When sending new email from that client, all works as expected. The email is relayed to the external smart-host and lands in external ISP Inbox. But for people who are using Outlook clients, sending new email to the disabled Mailbox account results in a "Delivery has failed to these recipients or distribution lists" message. The error is: IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+ 28FKODFHF45SPDLT+29_CN=RECIPIENTS_CN=myusername@company.com #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## My guess is that Outlook is caching a direct reference to the deleted user in the address book or elsewhere, causing routing to be ignored. Or maybe the issue is that Outlook references the remaining AD user account even though there is no more mailbox? Also the user is not receiving any email from exchange distribution lists. Any suggestions?
February 18th, 2010 8:44am

A bit more information. When I look in the Message Tracker I see that: Email sent from Outlook clients to the disabled Exchange mailbox have a recipient of: IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+ 28FKODFHF45SPDLT+29_CN=RECIPIENTS_CN=myusername@company.com Email sent from Outlook clients to normal Exchange mailboxes are just 'theusername@company.com' Email sent from Mac Mail clients to either enabled or disabled mailboxes have normal recipients like 'myusername@company.com'.
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February 18th, 2010 9:38am

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