Hi there, We use SBS 2008 which has Exchange 2007. I use the POP3 connector and smarthost feature which I know some people dont like but it works for us (and I dont think this problem is related to that). Our master domain name is e.g. name1.com. We have a user called Julie who has an email address julie@name1.com. Julie also wants to be able to send and receive emails for an email address with a different domain name julie@name2.com. This second email address already exists at our ISP so I just use the POP3 connector to download emails for julie@name2.com and send them to Julies account (e.g. julie@name1.com). So that Julie can send emails using julie@name2.com I cheat and just created a room booking mailbox in Exchange then changed its email address to julie@name2.com. I set send permissions on this so that user 'Julie' could send emails as julie@name2.com. I then changed the routing on julie@name2.com so that internal emails sent to this were forwarded to julie@name1.com. This has worked perfectly for several months but we decided last week that we wanted the 'cheating' email address to be on a stand alone PC that is not on the domain. I therefore removed the room booking mailbox julie@name2.com from Exchange. The julie@name2.com mailbox still exists at our ISP and I've set it up on another standalone PC under Outlook Express and it works fine. PROBLEM If anyone internally sends an email to julie@name2.com they get an error. But why? I have completely removed this email address from Exchange 2007. The domain name name2.com is not the same as the master domain name name1.com so staff should be able to send emails to julie@name2.com which should go out of the building to our ISP and then the standalone PC should download them. The standalone PC with julie@name2.com can receive emails from other people but not from users who were on the same network as julie@name2.com used to be on. I would understand why this would happen if the room booking email had the same domain name as the master domain. It would be because any emails sent to anyone@name1.com must exist on the domain, and if you remove an email address you cant send emails to it. However this room booking mailbox had a different domain name and becuase I've removed it the Exchange should just treat it as an external email address. Surely anyone@name1.com should be able to send an email to anyone@name2.com which is now an external email address. Where do I need to look or check to see if julie@name2.com still exists somewhere on my SBS 2008 or on Exchange 2007? Are there any clever commands I can type into the Exchange Command Line to show why this would happen? Any tips or advice (no matter how small) would be really appreciated.

Below is the error message. You can see the email is To: "julie@name2.com" from reception@name1.com>. I've just noticed the line below has the user name julie2. <IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Julie2@companyname.local> This is the user name for the room booking email I created. So, even though I've removed the room booking mailbox the system still thinks that julie@name2.com still exists somewhere. But where? --------------------------------------------- From: Microsoft Exchange Sent: 02 September 2010 14:01 To: Reception PC Subject: Undeliverable: test Delivery has failed to these recipients or distribution lists: julie@name2.com The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator. _____ Sent by Microsoft Exchange Server 2007 Diagnostic information for administrators: Generating server: IBM3400.companyname.local IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Julie2@companyname.local #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## Original message headers: Received: from IBM3400.companyname.local ([fe80::53d6:7687:33bc:582c]) by IBM3400.companyname.local ([fe80::64d6:7547:35bc:452c%10]) with mapi; Thu, 2 Sep 2010 14:00:38 +0100 Content-Type: application/ms-tnef; name="winmail.dat" Content-Transfer-Encoding: binary From: Reception PC <reception@name1.com> To: "julie@name2.com" <IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Julie2@companyname.local> Date: Thu, 2 Sep 2010 14:00:36 +0100 Subject: test Thread-Topic: test Thread-Index: ActKntYSWGqJRjPEQ0+de8x/Z3PjNg== Message-ID: <46A8D3DDFE00DC43AB6E3864FDD8369D01FDE089DD8E@IBM3400.companyname.local> Accept-Language: en-US, en-GB Content-Language: en-US X-MS-Has-Attach: X-MS-TNEF-Correlator: <46A8D3DDFE00DC43AB6E3864DDB8369D01FDE089DD8E@IBM3400.companyname.local> MIME-Version: 1.0

They are replying to an old message, so what they're replying to is the X.500-like address you see in the NDR (/O=FIRST ORGANIZATION/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23PDLT)/CN=RECIPIENTS/CN=Julie2@companyname.local). You can tell users to readdress the replies by selecting them from the address book. You can also add this address above (check the spelling to be sure I didn't make a typo) as a new address of type X500 (no period) to another user or contact to deliver replies somewhere, like a contact that points to the POP mailbox if that's what you want. Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Hi Ed, thanks for the reply. I'm fairly new to Exchange and sort of follow what you mean. You say that users are replying to an old message, but they are actually creating a new blank email and then typing in julie@name2.com which should now be an external email address (julie@name2.com is no longer appearing in the address book). As per my original post, if a user sends an email to julie@name2.com they get an error, but if they send an email to john@name2.com it works as john@name2.com is a valid email address at our ISP but was never on the domain (which remember is name1.com). Can you tell more about "You can tell users to readdress the replies by selecting them from the address book" as julie@name2.com is no longer in the address book. Any more help would be really appreciated. DL

Oh, and Julie2@companyname.local should no longer exist. I cant find it anywhere on the system but it was mentioned in the NDR.

On Fri, 3 Sep 2010 12:45:04 +0000, EssoOil wrote: > > >Hi Ed, thanks for the reply. > >I'm fairly new to Exchange and sort of follow what you mean. You say that users are replying to an old message, but they are actually creating a new blank email and then typing in julie@name2.com which should now be an external email address (julie@name2.com is no longer appearing in the address book). > >As per my original post, if a user sends an email to julie@name2.com they get an error, but if they send an email to john@name2.com it works as john@name2.com is a valid email address at our ISP but was never on the domain (which remember is name1.com). > >Can you tell more about "You can tell users to readdress the replies by selecting them from the address book" as julie@name2.com is no longer in the address book. > >Any more help would be really appreciated. Your NDR cites this as the reason for the inability to deliver the message: RESOLVER.ADR.ExRecipNotFound That "ExRecipNotFound" part tells me that the address (julie@name2.com in one case) is present as a legacyExchangeDN somewhere in Outlook. That could be in the O/R address of a message you're replying to, as a contact in the mailbox's Contact folder (perhaps the user added Julie to his Contacts from the GAL), or in Outlook's name cache. If Julie's a contact in the mailbox's Contacts folder, remove it. To clear the caches, see this: http://support.microsoft.com/kb/287623 --- Rich Matheisen MCSE+I, Exchange MVP --- Rich Matheisen MCSE+I, Exchange MVP

Hi, Since the Outlook clients use X500 address (legacyExchangeDN) to send the internal email, it's still use the old cache even though you delete the user account. You can test this issue in OWA. If that works, please try to clear the cache NK2 file on the Outlook side. Thanks Allen