Exchange 2007: Delivery has failed to these recipients or distribution lists
I am getting this error occasionally with a single internaluser. Most of the time I can email this user with no problems. I've tried deleting and recreating the mailbox. All mailboxes are on the same Exchange Server. Exchange 2007 All roles on one server Any tips on troubleshooting this error would be appreciated. Thanks! Subject: Undeliverable: Subject Delivery has failed to these recipients or distribution lists: '<User>'This recipient e-mail address was not found in the recipient e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the recipient 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: Servername.Orgname.corp IMCEAEX-_O=FIRST+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=user@domainname.com#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## Original message headers: Received: from Servername.Orgname.corp ([192.168.0.1]) by Servername.Orgname.corp([192.168.0.1]) with mapi; Thu, 14 Jun 2007 08:08:11 -0400Content-Type: application/ms-tnef; name="winmail.dat"Content-Transfer-Encoding: binaryFrom: User2 Displayname <user2@domainname.com>To: User Displayname<IMCEAEX-_O=FIRST+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=USER@domainname.com>Date: Thu, 14 Jun 2007 08:08:09 -0400Subject: FW: SubjectThread-Topic: SubjectThread-Index: AceufChByaDtH5NpQTmxmomcFNKoqAAAF2GgMessage-ID: <57E6EC8FBD32CD42BF9A9222569630FD056E90E3C2@Servername.Orgname.corp>Accept-Language: en-USContent-Language: en-USX-MS-Has-Attach:X-MS-TNEF-Correlator: <57E6EC8FBD32CD42BF9A9222569630FD056E90E3C2@Servername.Orgname.corp>MIME-Version: 1.0
June 14th, 2007 6:14pm

This is very weird. It looks like periodically Exchange tries to route this mesage outside of your organization. Check your Outlook nickname file (NK2) and maybe delete it.
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June 16th, 2007 2:30am

Thanks Jim, I'll check that out. I notice that if I manually address to user@domainname.com that it works without fail. What in my post is a clue to you that Exchange is trying to route outside? Does IMEAX indicate internet mail routing or some such? Thanks!
June 18th, 2007 3:50pm

Hi were you able to resolve this issue? we are having exactly the same issue. One thing what i notice, user gets an email internally from another user, and hit reply, outlook puts the username in quotes 'username' and if you double click to see details, you won't see any e-mail addresses linked to that name. usually if it finds the name in the address book, it will underline it. This is just happening randormly. Andy solution to this and why this is happening? any help will greatly appreciate. Delivery has failed to these recipients or distribution lists: 'user'This recipient e-mail address was not found in the recipient e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the recipient 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: server1 IMCEAEX-_O=FIRST+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=user@domain.com#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## Original message headers: Received: fromserver.domain.com ([192.168.12.1]) byserver.domain.com ([192.168.12.1]) with mapi; Wed, 4 Jul 2007 09:50:33+0800Content-Type: application/ms-tnef; name="winmail.dat"Content-Transfer-Encoding: binaryFrom:user <user@domain.com>To: 'user' <IMCEAEX-_O=FIRST+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=user@domain.com>Date: Wed, 4 Jul 2007 09:50:41 +0800Subject: FW: Message forwaredThread-Topic: Message forware Thread-Index: Ace9IfgkDeKHI/65Qgi0SJBMyyJpOAAu7uXgMessage-ID: 894C86DBED2F1E4F807264E1FF93650A118CD9D02D@server.domain.comAccept-Language: en-USContent-Language: en-USX-MS-Has-Attach:X-MS-TNEF-Correlator: <894C86DBED2F1E4F807264E1FF93650A118CD9D02D@server.domain.com>MIME-Version: 1.0
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July 4th, 2007 6:43am

I have seen this behaviour a fair few times when performing Exchange migrations. In my experience this behaviour occurs due to caching of a users old email address in Outlook. To resolve this you can try the following: Delete the Outlook clients nickname cache file by searching the local Outlook profile for a .NK2 file and deleting it. Change the Outlook tonon-cached mode to ensure it is not a cached entry from the OfflineAddress Book. Check the behaviour in OWA to confirm the server is generating the correct address list and has updated the GAL. Cheers, Rhys
July 4th, 2007 3:21pm

If you migrated the users from 2003 to 2007 doing a cross org migration, Migrating few users at the time.You will have that problem when users are replying to email that were recieved prior to the migration. The simplest way to resolve this problem is add a custom X500 address for each contact that refers to our olg org. /O=oldorg/OU=FIRST ADMINISTRATIVE GROUP/CN=RECIPIENTS/CN=userlias Hope this helps R
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September 11th, 2008 9:01pm

Hi: I deleted nk2, created a new profile, OWA is working fine with GAL, Outlook to non-cached, recreate the problem in other station creating new profile and added x500 address with /O=oldorg/OU=FIRST ADMINISTRATIVE GROUP/CN=RECIPIENTS/CN=userlias. Nothing Issue happens randomly, user can send to the users without any problem and users reply him without any problems but once a day or randomly users receive the NDR. thanks L
April 10th, 2010 5:32pm

Dear, Above stated problem can be seen due to multiple factors, may be client Cache is not updated, OAB and GAL is not downloaded/updated or LegacyExchangeDN is missing in the properties of those Mailboxes. you do the following and let me know the results: 1. Delete NK2 file on client side, re-download OAB and GAL from server and use non-cache (online mode) on Outlook, try to send email 2. Open ADSI Edit on the server, browse to the mailbox/contact and check whether LegacyExchangeDN, TargetAddress and ProxyAddress attributes are present? kindly post what is defined in all three attributes. further solution/troubleshooting will be Dependant on these attributes. Regards MYM
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April 10th, 2010 8:19pm

Hello All, Please check that the user is not a delegate of another user with an old account. That was my issue. Thanks!
May 12th, 2010 8:31pm

Hello All, Please check that the user is not a delegate of another user with an old account. That was my issue. Thanks! Can you elaborate on this? What do you mean by "old account". I have this issue with a couple users. And of course the 2 or 3 people out of my whole enterprise it is happening to are VIP's...
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May 13th, 2010 4:57pm

I am having the same problem. I had to remove and recreate a user's email address. After that I start getting it. It only happens internally, from the internal users. I already tried it on other internal user's outlook, I deleted his email address once you hit to send a new email and auto complete list finds it that time I hit the Delete button. After writing his address manually again just a second before I hit the send button his name underlined again, but I received the same error. So is there anything I have to change on the server or on the outlook who has the email issue? Thanks.
August 12th, 2010 6:52pm

We are experiencing a similar issue with one of our users. This user was newly created a couple months ago, and was not a migration. Others within Exchange are intermittently receiving a NDR when sending to this user: Delivery has failed to these recipients or distribution lists: 'User' 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: EX-CH-006-SV1.shared.exchangehost.com IMCEAEX-_O=IHOST_ou=Exchange+20Administrative+20Group+20+28FYDIBOHF23SPDLT+29_cn=Recipients_cn=user+5Fdomain+2Ecom@shared.exchangehost.com #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## We have made sure that the Outlook nk2 files are cleared and have even cleared the recent recipient list in OWA. As an additional bit of evidence that this is being caused server-side, we set up a new Entourage EWS connection on a computer that had never previously been connected to this domain. When a new message is created and the effected user's name is entered, the contacts and recent addresses suggestion window lists two entries for that user: one with his proper SMTP email address, and one with the X.500 address listed above. Is there anything we can check to try and find where this erroneous entry is coming from?
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September 23rd, 2010 8:50pm

On Thu, 23 Sep 2010 17:50:02 +0000, SWhitlow wrote: > > >We are experiencing a similar issue with one of our users. This user was newly created a couple months ago, and was not a migration. Others within Exchange are intermittently receiving a NDR when sending to this user: > > > >Delivery has failed to these recipients or distribution lists: 'User' 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: EX-CH-006-SV1.shared.exchangehost.com IMCEAEX-_O=IHOST_ou=Exchange+20Administrative+20Group+20+28FYDIBOHF23SPDLT+29_cn=Recipients_cn=user+5Fdomain+2Ecom@shared.exchangehost.com #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## > > > >We have made sure that the Outlook nk2 files are cleared and have even cleared the recent recipient list in OWA. > >As an additional bit of evidence that this is being caused server-side, we set up a new Entourage EWS connection on a computer that had never previously been connected to this domain. When a new message is created and the effected user's name is entered, the contacts and recent addresses suggestion window lists two entries for that user: one with his proper SMTP email address, and one with the X.500 address listed above. > >Is there anything we can check to try and find where this erroneous entry is coming from? That ExRecipNotFound error says the problem is with the O/R address in the message. That O/R address is the legacyExchangeDN property value at the time the message was sent. It's also the value that's stored in an Outlook Contact if you add a user from the AD as a Contact. For there to be a mismatch, the mailbox may have been deleted and the Exchange properties removed from the user. If another mailbox was created for the user it's very likely that an new legacyExchangeDN value was assigned to the user, especially if the mailbox remained, unpurged, in the mailbox database. --- Rich Matheisen MCSE+I, Exchange MVP --- Rich Matheisen MCSE+I, Exchange MVP
September 24th, 2010 2:47am

We are continuing to experience issues with this bounce re-occurring. We're actually seeing this occur in two separate domains, which are unrelated except for the common error that keeps coming up. So far it only seems to occur with one or two mailboxes in each domain. We have confirmed that none of these mailboxes were removed and recreated. One of the mailboxes was a migration from a different 2003 server, but I'm pretty sure the others were not. The circumstances of the error have made it incredibly difficult to track down. The problem is always intermittent; most messages will go through fine, and then one will bounce seemingly out of nowhere. Subsequent messages will often go through fine as well. We have removed the NK2 files and cleared the autocomplete cache many times. In most cases this seems to fix it for a while, but then it starts re-occurring a few weeks later. Bounces have occurred with messages sent from Outlook, OWA, and even Entourage. In the case of the Entourage message, the client was set up brand new for testing purposes, the autocomplete cache was cleared just in case, and the user's name was auto-completed from the GAL entry. We have checked each account in Exchange and only the proper SMTP address is listed (A legacyExchangeDN address was added at one point as a test, but it made no difference). At this point we're pretty baffled at the continual re-occurrence of the issue, and we have some pretty frustrated users. Any guidance would be appreciated.
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December 4th, 2010 5:32am

We are also experiencing this issue, when a user creates a cal appointment and sends it to a DL they are recieving a bounce but the user in the bouce was never part of the DL.
December 30th, 2010 8:35pm

We are also experiencing this issue, when a user creates a cal appointment and sends it to a DL they are recieving a bounce but the user in the bouce was never part of the DL. Make sure that the user listed in the bounce is not listed as a delegate for any of the users that are part of the DL. Also make sure that none of the DL user's have their calendars shared with that bounce recipient. I saw this exact circumstance before with another customer, and they swore up and down that they had removed the user from any DLs, shares and delegates. I loaded up Outlook for one of the DL members and sure enough, the removed user was listed as a delegate. Delegation and permissions do not get removed automatically when a user is removed from Exchange. http://www.vardynamics.com/
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December 30th, 2010 8:55pm

We have had the same issue and found that OWA works fine while Outlook will fail. An existing users mailbox is removed and recreated. Many are able to send to the user but others fail. I have found that the ones that fail are only those that have sent messages to that user previously and it only applies to Outlook not OWA. It seems like there are conflicting entries for the replaced mailbox in senders Outlook cache, so sometimes it goes thru, while other times it fails. Switching off cached exchange mode sometimes corrects the issue, but not in all cases. Replacing the Outlook profile of users who receive the message has corrected the issue each time so far. Hope this helps
January 7th, 2011 6:49pm

On Fri, 7 Jan 2011 15:49:48 +0000, goflyfishin wrote: > > >We have had the same issue and found that OWA works fine while Outlook will fail. > >An existing users mailbox is removed and recreated. Many are able to send to the user but others fail. I have found that the ones that fail are only those that have sent messages to that user previously and it only applies to Outlook not OWA. The value of the user's legacyExchangeDN property are different now to what they were before. The "address completion cache" on Outlook is the most common (but no the only) cause of this. You can make this symptom do away pretty easily by adding the old legacyExchangeDN value to the "E-Mail Addresses" tab on the user. Pick "X500" as the address type. >It seems like there are conflicting entries for the replaced mailbox in senders Outlook cache, so sometimes it goes thru, while other times it fails. Switching off cached exchange mode sometimes corrects the issue, but not in all cases. Replacing the Outlook profile of users who receive the message has corrected the issue each time so far. It may be the address completion cache, or it may be that the OAB hasn't been updated (or downloaded by the client), or that the problem happens when they reply to an e-mail sent by that mailbox before the legacyExchangeDN value changed. If the OAB is the problem you should address that. --- Rich Matheisen MCSE+I, Exchange MVP --- Rich Matheisen MCSE+I, Exchange MVP
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January 7th, 2011 11:03pm

Hi guys, I had the same issue with migrated users who we imported to our exchange server. The trick with nk2 file and checking the experience in OWA highlighted they were using outdated nicknames when sending emails. Also the point about delegate access; we had that for a different issue - Users who were imported from one exchange server, who had delegate access on their account had latent permissions on their account which were not showing up. We added delegate access again and then removed it; resolved all notification errors.
February 23rd, 2011 1:21pm

On Fri, 7 Jan 2011 15:49:48 +0000, goflyfishin wrote: > > >We have had the same issue and found that OWA works fine while Outlook will fail. > >An existing users mailbox is removed and recreated. Many are able to send to the user but others fail. I have found that the ones that fail are only those that have sent messages to that user previously and it only applies to Outlook not OWA. The value of the user's legacyExchangeDN property are different now to what they were before. The "address completion cache" on Outlook is the most common (but no the only) cause of this. You can make this symptom do away pretty easily by adding the old legacyExchangeDN value to the "E-Mail Addresses" tab on the user. Pick "X500" as the address type. >It seems like there are conflicting entries for the replaced mailbox in senders Outlook cache, so sometimes it goes thru, while other times it fails. Switching off cached exchange mode sometimes corrects the issue, but not in all cases. Replacing the Outlook profile of users who receive the message has corrected the issue each time so far. It may be the address completion cache, or it may be that the OAB hasn't been updated (or downloaded by the client), or that the problem happens when they reply to an e-mail sent by that mailbox before the legacyExchangeDN value changed. If the OAB is the problem you should address that. --- Rich Matheisen MCSE+I, Exchange MVP --- Rich Matheisen MCSE+I, Exchange MVP I know this is an old thread, but being this is the first time posting here, I am not sure how to find current threads yet. Your suggestion is something I wanted to try, but the address type only allows for SMTP. How can I change this? "The value of the user's legacyExchangeDN property are different now to what they were before. The "address completion cache" on Outlook is the most common (but no the only) cause of this. You can make this symptom do away pretty easily by adding the old legacyExchangeDN value to the "E-Mail Addresses" tab on the user. Pick "X500" as the address type." Edited to add that the issue is resolved. Your advice worked, my understanding of how to include an X500 address wasw the final hurdle to overcome.
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August 31st, 2011 4:41pm

have been running into this same issue with one user in my org. I migrated from 2003 to 2007, and slowly, for different users in my domain, the nk2 file/autocomplete keeps trying to send mail to a mailbox that was briefly set up, then deleted, as I misspelled the users last name. I honestly have no idea how the two mailboxes have been linked, and it is driving me insane, as I have been all through ASDIEdit looking for the old value of the misspelled entry, and I cannot find it. Here is the laundry list of where I am at/detailed description: valid username is jdoe, old misspelled entry is gdoe (obviously sanitized) Problem is when users pull from GAL/Outlook autocomplete, Outlook shows jdoe@domain.com, but exchange tries to send it to gdoe@domain.com gdoe is not associated with the user in ASDIEdit under LegacyExchangeDN I have assigned the user an x500 address of gdoe, no avail. I have tried deleting nk2 files, moving the GAL server around, set users to not run outlook cached mode, redownloaded the OAB, and still nothing. Once a user has the missasociated address, they are unable to email the proper address, unless they use an alias that I have set up. Can anyone point me to a tool that will scrape all of ASDIEdit for a value, so maybe I can find where this rogue entry lives?
September 16th, 2011 6:44pm

did you update the GALs and OABs?
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September 17th, 2011 8:24pm

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