Home > Exchange 2007 > Exchange 2007: Delivery has failed to these recipients or distribution lists

Exchange 2007: Delivery has failed to these recipients or distribution lists

Two weeks ago client called me and was screaming that he has clients facing problem with their mail.

The error when we sent mail to them was:

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.domainname.com 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.domainname.com ([192.168.3.20]) by Servername.domainname.com([192.168.0.1]) with mapi; Fri, 11 April 2008 06:24:22 -0400
Content-Type: application/ms-tnef; name=”winmail.dat”
Content-Transfer-Encoding: binary
From: User2 Displayname <user2@domainname.com>
To: ‘User Displayname’
<IMCEAEX_O=FIRST+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP

_CN=RECIPIENTS_CN=USER@domainname.com>

The users have valid mailboxs and all the rest are alright.

After some times I discovered that the system admin disconnect those clients before and recreate their mailboxs instate of reconnect them.

so I made small test .. open my OWA and send those users mail… so guess what happen??? yes.. they got it.

the problem is that the rest of users are caching the old accounts and is using autocomplete in Outlook, which is resolving to the old e-mail address
because their cache has that old address, The OWA do not cache names so I can send via it to users new mailbox.

So what is the solution?? It can be done by two ways:

1- Delete current mailboxs and create users accounts and reconnect them .

2- Outlook maintains a “nickname” list that is used by both the automatic name checking and the AutoCompletion features. The nickname list is automatically compiled as you address email messages. If the nickname cache becomes corrupt, Outlook may not be able to identify recipients, may offer incorrect recipients, may send to an incorrect or old email address, or may send the message to the wrong person.

If you are having problems with a single recipient, you can easily delete the one cached entry as shown in the following section, “Delete a single cached entry”. Otherwise, proceed to the section titled “To delete your Nickname Cache file” further below.

To delete a single cached entry
  1. Open Outlook
  2. Open a new message window; go to the File menu and choose New – Mail Message.
  3. Type one or more letters of the recipient name or address; this will show memorized (cached) entries in a drop-down list. Use the arrow keys on your keyboard to select the entry to be deleted. With the entry highlighted, press the DEL or DELETE key or your keyboard.

This removes the entry from your autocompletion cache.

To delete your Nickname Cache file.

Use the following steps that are appropriate for your version of Microsoft Windows to reset the Outlook nickname cache. After you restart Outlook, Outlook generates a new nickname cache.

Microsoft Windows XP

  1. Exit Outlook.
  2. Start Microsoft Windows Explorer.
  3. On the Tools menu, click Folder Options, and then click the View tab.
  4. Under Advanced Settings, select the Show hidden files and folders check box.
  5. Click OK.
  6. Click Start, point to Search, and then click All files or folders.
  7. In the Search Companion box, type *.NK2 in the All or part of the file name box.
  8. In the Look in box, select your local hard disk drive.
  9. Click Search.
  10. Right-click the .NK2 file with the name of the profile that you want to reset, and then click Rename.
  11. Rename the file to profile name.bak, and then press ENTER.
  12. Exit Windows Explorer.
  13. Restart Outlook.
  1. Microsoft Windows Vista

Exit Outlook
Click the Start Menu
Click Search
Click Advanced Search
Check the box for ‘Include non-indexed, hidden, and system files (might be slow)
Search for *.NK2 in the ‘Name’ field

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    1. Ethan Russell
      July 17, 2008 at 3:13 am

      This is correct to some extent. I’ve run into the exact same scenario, sadly I’ve come to realize something about deleting the cached nicknames in Outlook… the problem can possibly return. If the user has any old emails, meetings, etc. that pointed to the old user object in AD which they then forward or reply to, the nickname cache inserts the old invalid entries into the nickname list again. I would love to find a more comprehensive solution to this issue.

    2. Tony V.
      July 17, 2008 at 5:33 pm

      I was having the same problem with a user. I did what you suggested in clearing out the cache and that worked on everyone except one user. She still can not send mail to the one user that had been deleted. I have even deleted her Outlook.ost file so that it could get recreated. Any other suggestions would be appreciated.

    3. Mohamed Fawzi
      July 17, 2008 at 10:50 pm

      try first to send from her account to that user using OWA.

    4. August 16, 2008 at 12:09 pm

      Your blog is interesting!

      Keep up the good work!

    5. Brian
      September 25, 2008 at 3:39 pm

      I agree with Ethan (Comment 1). Is there a way to setup exchange to forward the old DN name to a correct smtp address?

      The discription and the possible solution are very well laid out thank you.

    6. Chris Zvolensky
      February 3, 2009 at 5:03 pm

      I don’t think deleting the .NK2 file or an entry from the .NK2 file will work. At least it didn’t in my case. I had to delete the actual contact from the user’s Contacts folder. Then the next time they email that person it will pull from the GAL.

      My current problem is that OWA does seem to have a cache and I’d like to know where it is and how to clear it.

    7. Chris Zvolensky
      February 3, 2009 at 5:17 pm

      Nevermind, I just found an answer to my question regarding the OWA cache: While typing an address in the “To” field, you can arrow up or down to highlight the bad address, then hit the Delete key.

    8. Mohamed Fawzi
      March 24, 2009 at 10:57 pm

      by the way I think there is another workaround to give user disconnected mailbox SID to the new user

    9. April 15, 2009 at 4:54 pm

      Hey, cool tips. I’ll buy a bottle of beer to that man from that forum who told me to go to your blog :)

    10. May 1, 2009 at 2:44 am

      I have the exact same issue for 3 of my users. However, the solution doesn’t seem to be in the caching. I had to delete the user accounts and re-create them and import the old mail back in. I then went in and added the aliases for the users that they needed. We use a first name last initial alias structure, but some people still try just first name or first initial last name etc. So we add all viable options of names to the email address tabs. These users STILL are not receiving mail at the old username alias. One user account was simply the first name, and to bring her up to the current standard the new account was first name last initial then the alias of first name was added. Doesn’t work. Anyone have any answers?

    11. Jamie
      August 25, 2009 at 9:01 pm

      Had the same issue and clearing the cache worked beautifully. Thanks for the post.

    12. Dolores
      October 23, 2009 at 7:05 pm

      Yesterday I had a similar problem. We are running Exchange 2007 SP1 and all clients are Outlook 2007 in cached mode. I got the solution from one coworker:
      The cached entries in Outlook autocomplete lists reference LegacyExchangeDN linked to now disconnected mailbox. New mailbox has a different ExchangeLegacyDN so when AD tries to findout recipientinformation based on the ExchangeLegacyDN sent by Outlook, it will fail and return message that “the recipients email address was not found in the recipient’s email system”. The solution is to create an x500 email address with value of ExchangeLegacyDN listed in the diagnostics information provided by the bounced NDR message. For example my NDR contained the following line:
      IMCEAEX_O=MYCOMPANY_OU=US01+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=UID@internal.mycompany.com
      #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

      With this information we created an X500 address that will help AD resolve the old ExchangeLegacyDN and avoid bounces. For timing purposes we force the generation of OAB so that next time that clients downloaded the OAB it will contain the new information for the user. Based on the info returned in the NDR, the x500 created was:
      /o=mycompany/ou=US01 Administrative Group/cn=Recipients/cn=uid

    13. Dolores
      October 23, 2009 at 7:08 pm

      Yesterday I had a similar problem. We are running Exchange 2007 SP1 and all clients are Outlook 2007 in cached mode. I got the solution from one coworker:
      The cached entries in Outlook autocomplete lists reference LegacyExchangeDN linked to now disconnected mailbox. New mailbox has a different ExchangeLegacyDN so when AD tries to findout recipientinformation based on the ExchangeLegacyDN sent by Outlook, it will fail and return message that “the recipients email address was not found in the recipient’s email system”. The solution is to create an x500 email address with value of ExchangeLegacyDN listed in the diagnostics information provided by the bounced NDR message. For example my NDR contained the following line:
      IMCEAEX_O=MYCOMPANY_OU=US01+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=UID@internal.mycompany.com #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

      With this information we created an X500 address that will help AD resolve the old ExchangeLegacyDN and avoid bounces. For timing purposes we forced the generation of OAB so that next time that clients download the OAB it will contain the new information for the user. Based on the info returned in the NDR, the x500 created was:
      /o=mycompany/ou=US01 Administrative Group/cn=Recipients/cn=uid

      • Ai Ling
        October 29, 2009 at 12:12 am

        Hi Dolores,

        No, it didn’t work for me.
        i created x500 using the diagnositic value eg… IMCEAEX_O…. but email still bouncing back. Do i need to run any update?

        Thanks

      • January 18, 2013 at 4:23 pm

        Thank you so much! This is a much better solution given this can be done ONCE from AD and doesn’t involve going to individual machines, but this solves any weird issues of the address showing back up in the cache! Best answer!! =D

    14. March 28, 2010 at 1:35 pm

      well, i had the same issue whe I try to send emails to one specific SMTP domain.
      i got it then when i discovered that domain was added to the accepted domain in my exchange.

      simply i removed it and all works

    15. Zahirul alam
      April 23, 2010 at 1:24 am

      Excellent posting… I was having the same exact issue and scratching my head off wondering what went wrong.

    16. Anonymous
      June 28, 2010 at 1:17 pm

      Just to let you know I had the same problem and I just cleared offline contacts from Outlook 2010 (Contact folder properties – “Clear offline items”) and when they sync’d back a few minutes later from the BPOS server it worked again.

    17. fredo
      October 28, 2010 at 8:03 pm

      Windows Button –> Run Command

      outlook /cleanautocompletecache

    18. November 15, 2010 at 6:32 pm

      Thanks, deleting the n2k files did it for me…

    19. Amir
      April 10, 2011 at 10:06 am

      Thanks, it worked for me

    20. Avani
      December 1, 2011 at 2:11 pm

      i didnt have n2k file at all……………what to do?

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    23. Den
      January 25, 2012 at 9:02 am

      Work really well. Thank you for posting it.

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    27. September 4, 2012 at 12:05 am

      So, i stumplet across this blog when i had this problem, however i didn’t find a solution here i could use, so i will share the one solution that did work for me so it hopefully can help someone else to :)

      This solution should work in Windows Vista and Windows 7 with Outlook 2010 and outlook 2007, i haven’t tried it in any other OS.

      start explorer –> browse to the following location:
      C:\Users\\AppData\Local\Microsoft\Outlook\Offline Address Books. When you are at this destination, you will find a folder called something like “effe455b-f0b5-4d96-3fef-5873b246289c” When you have found this folder, delete it. Start outlook again and try to send to the mailbox again, the problem should now be solved.

      As always, i recommend you to take a backup of the folder, just in case something should go wrong however i have done this on about 10 computers now with no problems.

      It is important to mention that this don’t delete any entries in their rapid contact list, so your users won’t even notice the change :)

      Have a nice day

      \\Martin T

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