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outlook 2003 mail delivery failed for Active Directory user RRS feed

  • Question

  • Server 2003/Exchange2003

    We are using an outside company (Integra) to handle our email and only use Exchange for shared archived email.

    When configuring active directory users the wizard automatically sets up email entries in the format: Username@PKA.local

    When responding to a meeting invite from outlook to a local AD user, all users receive undeliverable messages for the accounts in the format Username@PKA.local as below...

    The example below was a bounce back when I accepted the invite.  The invite shows up on my calendar just fine.

    This message was created automatically by mail delivery software.

    A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es) failed:

      miguel@PKA.local
        Unrouteable address

    ------ This is a copy of the message, including all the headers. ------

    Return-path: <kevin@pkarchitects.net>
    Received: from wsip-70-166-120-183.ph.ph.cox.net ([70.166.120.183] helo=PK01)
        by arelay1 with esmtpa (Exim 4.72)
        (envelope-from <kevin@pkarchitects.net>)
        id 1W8D9b-0001kB-24
        for miguel@PKA.local; Tue, 28 Jan 2014 10:12:56 -0800
    From: "Kevin Simmons" <kevin@pkarchitects.net>
    To: "miguel saucedo" <miguel@PKA.local>
    Subject: Accepted: Miguel Chaperone School
    Date: Tue, 28 Jan 2014 11:13:05 -0700
    Message-ID: <398EA47278F54C9FA9CFFB725FD6C079@PK01>
    MIME-Version: 1.0
    Content-Type: text/calendar; method=REPLY;
        charset="utf-8"
    Content-Transfer-Encoding: 7bit
    X-Mailer: Microsoft Office Outlook 11
    Thread-Index: Ac8cSpjUhKBGTbBKQt+PScNbb6MWwAABfTJgAABJyYAAALiiEA==
    X-MimeOLE: Produced By Microsoft MimeOLE V6.3.9600.16384

    BEGIN:VCALENDAR
    PRODID:-//Microsoft Corporation//Outlook 11.0 MIMEDIR//EN VERSION:2.0 METHOD:REPLY BEGIN:VEVENT ORGANIZER:MAILTO:/o=PKArchitects/ou=First Administrative
      Group/cn=Recipients/cn=miguel
    DTSTART:20140206T070000Z
    DTEND:20140208T070000Z
    LOCATION:Flagstaff
    TRANSP:OPAQUE
    SEQUENCE:3
    UID:040000008200E00074C5B7101A82E00800000000102573EC0F1CCF010000000000000000100
     0000037C3D09157000340AA5D3F23F6A60078
    DTSTAMP:20140128T181305Z
    SUMMARY:Accepted: Miguel Chaperone School
    PRIORITY:5
    X-MICROSOFT-CDO-IMPORTANCE:1
    CLASS:PUBLIC
    ATTENDEE;PARTSTAT=ACCEPTED:MAILTO:kevin@pkarchitects.net
    END:VEVENT
    END:VCALENDAR

    Thursday, January 30, 2014 2:48 PM

Answers

All replies

  • You say that your mail is managed by an external company.  I believe they will need to assist you with this issue.
    Thursday, January 30, 2014 3:55 PM
  • We have outlook configured for 2 accounts:

    A pop email server

    and

    an exchange server

    The exchange server Active Directory user profile lists the email for each entry in the format: Username@PKA.local

    I am wondering if the creation of the AD user profile and assignment of the email address by the AD add user wizard actually creates an exchange email account?  or just points to one that may in fact not exist.  If this is the case - can I just delete or revise the entry under each user to reflect the pop email account?

    As I said before we are not using exchange for anything but common email archival.

    Thanks

    Thursday, January 30, 2014 4:40 PM
  • If you have two MAPI providers in one profile it rarely works well. In this case it looks like Outlook is using the ISP as a SMTP relay and trying to send e-mail to a ".local" domain -- most likely because you're picking the recipient out of the GAL or OAB and that's the primary SMTP address assigned to them.

    You have to create mail-enabled Contacts for the "real" addresses and send the e-mail to them instead of the mailboxes.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Thursday, January 30, 2014 9:20 PM
  • No MAPI accounts at all...

    1 pop/smtp account through integra which is the default

    2 exchange

    The problem occurs when any of us receive an invite and we accept it.  The event goes onto the local outlook calendar, and we get the bounce back as undeliverable to the exchange server.

    A little history - we recently rebuilt the 2003server installation.  Before the rebuild, with the same internet/email configuration, we did not experience this.  So apparently something is new about the rebuild configuration and I suspect we never had the active directory component previously as we do now.  Either that or a policy was in place that governed the AD user creation that prevented this behavior.

    I have since inherited this and need to dial in what is happening.

    Any help is appreciated!

    Thursday, January 30, 2014 10:26 PM
  • Exchange is a MAPI account.  Rich is right about what is likely happening.  You say you rebuilt the environment - if you had things working, then the environment failed and you relied on the POP3 system, you changed the primary delivery system to POP3 (since the Exchange system wasn't able to deliver).  Try changing the default delivery location in your Outlook profile to the Exchange service and see what that does.
    Friday, January 31, 2014 1:26 PM
  • Ok, I didn't know that exchange was MAPI...

    The reason the server was rebuilt was that the hard drive on the previous build failed.

    However, we never were using exchange as the default - it has always been a pop server - and that has not changed.  The only thing that has changed is the server and the user profiles in AD that were rebuilt.  The previous build was done by a vender 7 or 8 years ago and there were no doubt policies in place which set up the users in such a way as to prevent this. That vender was shady and stole our licenses then disappeared - so no help there.

    The answer must be in the profiles or some other settings on the server.

    Question: does the creation of an AD user automatically create an exchange email account?

    If not then that is why the email is undeliverable to Username@PKA.local

    Friday, January 31, 2014 2:33 PM
  • Creating an AD user doesn't create a mailbox automatically unless you use the Exchange ADUC (not the default Windows one under Administrative Tools) to create the account.
    Friday, January 31, 2014 6:09 PM
  • Are sending an acknowledgement back to the meeting originator when you accept the invitation? If so, Outlook's sending that to the ISP.

    Does this happen if you accept a meeting and deal with it in the same way using OWA?

    If you were running Exchange 2003 before you certainly had that "Active Directory component". Exchange can't even be installed without it. :-)

    How about some information about the original message (i.e. the meeting request). Was the sender in that ".local" domain or some other domain? Use the message tracking log to discover that. If you can't find the outbound message in there then it's possible that our Outlook clients are using the ISP's SMTP relay server directly.

    Also, in what domains are you creating SMTP addresses? And what domains are in your Recipient Policies and are they marked as "This Exchange organization is responsible . . ."?

    I'm assuming that your Outlook clients are using YOUR Exchange server as their SMTP server. Is that correct?


    --- Rich Matheisen MCSE&I, Exchange MVP

    Friday, January 31, 2014 8:19 PM
  • No, the creation of an AD user doesn't automatically assign a mailbox to that user. When you use the ADUC to create a user and the machine on which you're running the ADUC has the Exchange Management Tools installed on it, you'll receive an additional dialog box asking if you want to "Create an Exchange mailbox". If you just accept the default, the box in the upper left-hand corner will be checked and a mailbox will be assigned.

    However, that's not the end of the mailbox creation process. Exchange 2003 has a pair of Recipient Update Services. There's one for the "Enterprise" and one for the "Domain". Make sure they're both directed to a domain controller and that the Microsoft System Attendant service is running. Verify that there are no errors being recorded in the server's Application event log. If the RUS isn't working then no mailbox will be created even if you tell the ADUC you want on to be.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Friday, January 31, 2014 8:28 PM
  • Ok,

    Let me ask a 'ridiculous' question...

    Can I revise the AD user profile to redirect the email to the Integra pop email address so that there is no traffic being sent to the exchange email we are not wanting to use?

    We only want to use the exchange server for group storage / access of archived emails, and do not want to have exchange email accounts.

    Does that make sense?

    Monday, February 3, 2014 2:13 PM
  • As a test perhaps I could send you an meeting invite and you can try to reply and see what kind of bounce back message you get.

    That might help resolve this.

    Monday, February 3, 2014 2:27 PM
  • The method used to create users is on the Start menu under Programs click under Microsoft Exchange - click Active Directory Users and Computers - right click New User and fill in the user name, password, and set passwords etc.  This automatically fills in the Username@PKA.local email address.

    Question:  How do I check to see if an Exchange email address in fact exists? Manage the inbox/settings etc if so?

    I  can't find out how to access the 'email tracking log'.  Is this something that has to be done through outlook? or on the server?

    Below is the text of the most recent bounce back I have received.

    This message was created automatically by mail delivery software.

    A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es) failed:

      miguel@PKA.local
        Unrouteable address

    ------ This is a copy of the message, including all the headers. ------

    Return-path: <kevin@pkarchitects.net>
    Received: from wsip-70-166-120-183.ph.ph.cox.net ([70.166.120.183] helo=PK01)
        by arelay1 with esmtpa (Exim 4.72)
        (envelope-from <kevin@pkarchitects.net>)
        id 1W8D9b-0001kB-24
        for miguel@PKA.local; Tue, 28 Jan 2014 10:12:56 -0800
    From: "Kevin Simmons" <kevin@pkarchitects.net>
    To: "miguel saucedo" <miguel@PKA.local>
    Subject: Accepted: Miguel Chaperone School
    Date: Tue, 28 Jan 2014 11:13:05 -0700
    Message-ID: <398EA47278F54C9FA9CFFB725FD6C079@PK01>
    MIME-Version: 1.0
    Content-Type: text/calendar; method=REPLY;
        charset="utf-8"
    Content-Transfer-Encoding: 7bit
    X-Mailer: Microsoft Office Outlook 11
    Thread-Index: Ac8cSpjUhKBGTbBKQt+PScNbb6MWwAABfTJgAABJyYAAALiiEA==
    X-MimeOLE: Produced By Microsoft MimeOLE V6.3.9600.16384

    BEGIN:VCALENDAR
    PRODID:-//Microsoft Corporation//Outlook 11.0 MIMEDIR//EN VERSION:2.0 METHOD:REPLY BEGIN:VEVENT ORGANIZER:MAILTO:/o=PKArchitects/ou=First Administrative
      Group/cn=Recipients/cn=miguel
    DTSTART:20140206T070000Z
    DTEND:20140208T070000Z
    LOCATION:Flagstaff
    TRANSP:OPAQUE
    SEQUENCE:3
    UID:040000008200E00074C5B7101A82E00800000000102573EC0F1CCF010000000000000000100
     0000037C3D09157000340AA5D3F23F6A60078
    DTSTAMP:20140128T181305Z
    SUMMARY:Accepted: Miguel Chaperone School
    PRIORITY:5
    X-MICROSOFT-CDO-IMPORTANCE:1
    CLASS:PUBLIC
    ATTENDEE;PARTSTAT=ACCEPTED:MAILTO:kevin@pkarchitects.net
    END:VEVENT
    END:VCALENDAR

    Monday, February 3, 2014 2:53 PM
  • Can you explain why you need to use the ISP's SMTP relay server?

    You're really asking a question about the Outlook e-mail client, not Exchange.

    If you're using Outlook 2013 you can have multiple accounts in the same profile, which sounds more like what you're trying to do. As I said before, trying to get Outlook to handle multiple access methods with only one account (i.e. mailbox) usually ends in tears.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Monday, February 3, 2014 3:00 PM
  • Rich,

    Forgive my ignorance, but how do you check to see if a mailbox exists in exchange - I don't see anything to do this nor manage them.  Maybe there are none  to manage?

    Is there a good guide to use for setting up new users in AD/Exchange so I can get a handle on what should have been done versus what was done?

    Thanks

    Thursday, February 6, 2014 2:11 PM
  • Using the Exchange System Manager would be a good place to start.

    Navigate your way to the Administrative Groups, then to the specific Administrative Group, then to the Servers container, then to the Server, then to the Storage Group, then to the Mailbox Store, and beneath that to the Mailboxes.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Thursday, February 6, 2014 5:00 PM
  • ok got that.  I had almost figured that out but not dug deep enough.

    So some users have a huge file size like 3,325,556KB while mine for instance has 4KB.  Is there no way to go into the mailbox and see the contents?

    Are all the relevant settings on the AD User object or is there some other place where the mailbox settings live?

    Lastly, how do changes to the email address listed under the AD User object get pushed to the Global Address list?  Do I have to reboot the server to rebuild that list?  or will rebooting the client workstation pull a fresh copy on startup?

    Thanks again.

    Thursday, February 6, 2014 9:01 PM
  • I have made changes to the AD Users 'General' Tab and the revised address shows up in the 'E-mail Addresses' Tab entry as Primary.  Restarted the Server, and workstation, but when I look up the corresponding entry in the Global Address Book - it remains unchanged.

    How do changes propagate?  Do I have to re-create the user?

    Obtuse - definition? MicroSoft

    Friday, February 7, 2014 1:18 PM
  • An administrator has no permission (at least not by default) to open another mailbox to examine its contents. That's not to say you can't give yourself Full Mailbox Access to a mailbox and use wither OWA or Outlook to open one.

    For Exchange 2003 everything that's specific to that user and their mailbox is a property of the AD user object. Some of those properties are pushed to the mailbox on the Exchange server (mailbox permissions, for example). Others (say, in the absence of a specific value) are inherited from with the parent AD structures or from the mailbox database (which is really another AD object in the configuration naming contest of the AD).

    The AD is the Global Address List. Any changes you make are immediately available on the Domain Controller where the changes were made, but may be note be visible on other DCs either due to propagation delays or problems with AD replication.

    OTOH, the Offline Address Book is, by default, generated only once each day. Assuming the OAB generation isn't failing, the changes will be downloaded by the Outlook client, usually the next time the user logs on to the mailbox.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Friday, February 7, 2014 7:51 PM
  • Assuming your Outlook client is NOT using "cached mode" the changes should be seen soon after they're made. OTOH, if you ARE running Outlook in cached mode those change won't usually show up until the following morning.

    --- Rich Matheisen MCSE&I, Exchange MVP

    Friday, February 7, 2014 7:54 PM
  • Well it looks like none of our outlook installations actually are accessing the exchange email, nor are we able to send to those email addresses even though they exist.  I have 2 email inboxes in Outlook, 1 is the Integra inbox - works fine.  The other is called Mailbox - UserName - populated with folder that are and always have been empty.  If I send an email to myself at kevin@PKA.local  I get the following bounce back.

    This message was created automatically by mail delivery software.

    A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es) failed:

      kevin@pka.local
        Unrouteable address

    ------ This is a copy of the message, including all the headers. ------

    Return-path: <kevin@pkarchitects.net>
    Received: from wsip-70-166-120-183.ph.ph.cox.net ([70.166.120.183] helo=PK01)
        by arelay2.integra.engr with esmtpa (Exim 4.72)
        (envelope-from <kevin@pkarchitects.net>)
        id 1WBtMM-0005N1-Gr
        for kevin@pka.local; Fri, 07 Feb 2014 13:53:18 -0800
    Reply-To: <kevin@pkarchitects.net>
    From: "Kevin Simmons" <kevin@pkarchitects.net>
    To: <kevin@pka.local>
    Subject: test
    Date: Fri, 7 Feb 2014 14:53:18 -0700
    Message-ID: <F708D49EB6A64BE69891BF9C7B528529@PK01>
    MIME-Version: 1.0
    Content-Type: multipart/related;
        boundary="----=_NextPart_000_0050_01CF2414.572804A0"
    X-Mailer: Microsoft Office Outlook 11
    Thread-Index: Ac8kTwKRc8hlRKNXSlye9E4r5UyfJQ==
    X-MimeOLE: Produced By Microsoft MimeOLE V6.3.9600.16384

    This is a multi-part message in MIME format.

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    test
     

    Thanks!

     

    Kevin Simmons

    Project Manager

     



    4515 S McClintock Dr. Suite 206

    Tempe, Arizona 85282

    p 602 283 1620

    f 602 283 1621

    c 480 702 9687

    kevin@pkarchitects.net

     

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    ------=_NextPart_000_0050_01CF2414.572804A0--

    beyond that - the Global Address Book does not update!

    Friday, February 7, 2014 9:57 PM
  • Well, of course, you get a NDR when you send to an e-mail address with a ".local" top-level domain and use your ISP as the SMTP relay. Nobody can find that domain name in an Internet-facing DNS -- which is exactly what the error message says.

    If you want to know how to make this sort of thing work you'll have to explain how your e-mail clients are used (are then used only from within your LAN or VPN, or are they used from "outside" your network), whether or not you expect those clients to send e-mail anonymously or should they authenticate (and consider the strength of your user's passwords!)

    Rather than jump through all the hoops of having two mailboxes for each person, have you considered using something like Office 365? You can lose your old Exchange server and just move everything to a platform that allows you to have pretty large mailboxes. The only thing you won't get are Public Folders (at least not yet). But I'm guessing you don't use them anyway.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Friday, February 7, 2014 10:21 PM
  • Well in fact the ONLY reason we use the Exchange server is for shared folders - we archive all of our project specific emails so we can all access them and keep them archived for legal purposes.

    Apparently something is not configured correctly - I think when the new machine was built we lost a policy that probably set the new AD user's primary email address to Username@pkarchitects.net instead of Username@PKA.local

    I have changed the primary email address in the AD user objects but the changes are not propagating to the Global Address book.

    I have figured out that office 2013 is what we need to get, but if the exchange server is not configured properly then I will still be experiencing these issues.

    Thanks for your patience!

    Friday, February 7, 2014 10:40 PM
  • Outlook 2003 turns on cached mode by default.  I turned it off and the changed propagated.  So at least that is solved.  In this configuration should it be off on all the systems?  I do not have any roaming users accessing exchange remotely.

    Thx

    Friday, February 7, 2014 11:06 PM
  • Progress at last - with the changes to the Global Address List in place when I send a Calendar invite and use the updated entry (not the one in autocomplete) then there are no errors or bounce back messages for either the sender nor the recipient when confirming etc.

    Why would the autocomplete version usually just typed in i.e. Kevin@pkarchitects.net versus the GAL version behave differently?  The problem goes away if I manually delete the old autocomplete entry and let it create a new one from the GAL, but just curious.

    Thx

    Friday, February 7, 2014 11:28 PM
  • "An administrator has no permission (at least not by default) to open another mailbox to examine its contents. That's not to say you can't give yourself Full Mailbox Access to a mailbox and use wither OWA or Outlook to open one."

    What is OWA?

    How do I give the Adminstrator login full mailbox access.  I really need to figure out what is locked away in some of these accounts.  Then address the issue of why the 'Mailbox' entry in the Outlook tree view is devoid of content.

    Friday, February 7, 2014 11:50 PM
  • After making the change to the recipient policy did you applyclick the policy and select "Apply this policy now...".

    You can check the e-mail addresses assigned to each mailbox by looking at the user's property page and selecting the "E-mail Addresses" tab -- after you apply the recipient policy.

    FYI, using the recipient policy to give mailboxes a new SMTP address won't remove the SMTP address already assigned to that mailbox. The current primary e-mail address will be demoted to a secondary e-mail address (it will not be displayed in a bold font) and a new primary address will be assigned. If you must remove the old address you can use admodify to do that pretty quickly.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Saturday, February 8, 2014 2:40 AM
  • Well, nothing "propagated". You're looking at the GAL (which is really a live view of the AD) when you're not in cached mode. When you area local copy of the GAL.

    If the changes are not showing up by the following day you may have a problem with the Offline Address Book generation process. To see more detail, set the Diagnostics Logging level on the server that is the OAB generation server to "Medium". The service is MSExchangeSA and the category is "OAL Generator". Then find the OAB, right-click it and select "Rebuild". Check the Application event log afterwards and correct any errors -- then rebuild the OAB again.

    Once you know you have a current OAB you can shut down your Outlook client, find the *.OAB files on your client machine, restart Outlook and force a download of the OAB.


    --- Rich Matheisen MCSE&I, Exchange MVP

    Saturday, February 8, 2014 2:49 AM
  • When you built the new server did you change the name of the Exchange organization?

    Outlook (using the OAB, and the GAL) uses the legacyExchangeDN (LDN) as the sender or recipient identification (to be backwards-compatible with old versions of Exchange and so you can reply to messages even if you alter every one of the E-mail addresses on the mailbox. If the old LDN wasn't the same as the new LDN then you may encounter problems such as the one you're experiencing.

    The Outlook autocomplete cache can be an evil thing. :-)


    --- Rich Matheisen MCSE&I, Exchange MVP

    Saturday, February 8, 2014 3:00 AM
  • OWA == Outlook Web Access. It's a browser-based way to access your mailbox.

    To assign Full Mailbox Access to individual mailboxes:
    http://support.microsoft.com/kb/268754/en-us

    To give one account access to ALL mailboxes in a database:
    http://support.microsoft.com/kb/821897/en-us


    --- Rich Matheisen MCSE&I, Exchange MVP

    Saturday, February 8, 2014 3:09 AM
  • I followed the article to give access to all mailboxes but don't see how to access the content.

    Tuesday, February 11, 2014 2:26 PM
  • You use Outlook, or OWA.

    --- Rich Matheisen MCSE&I, Exchange MVP

    Wednesday, February 12, 2014 3:01 AM
  • From what I can see to use OWA I have to make changes to he server to enable it - is that correct?

    When you say use Outlook - do you mean install it on the Server? or do I have to set up outlook on a workstation and configure it to connect to each individual account just to review what is in there and determine if I can delete it etc

    I thought that giving admin access to the email was going to allow me to manage the content in the accounts on the server - otherwise what is the point of changing the rights?

    On my system I have outlook 2003 running and have a Personal Folders section, Mailbox section, and Public Folders section.  The Mailbox section is empty - always has been - yet the server shows 4kb of data - I need to see what that is - how?  Outlook does not see it.  The only thing I can think it would be has to be related to favorites on the Public Folder side.  Does that make sense?

    Say for instance that there is an email that is crashing a users outlook when he attempts to download it - what would the procedure be to go into the server and delete the offending message?

    Thx

    Wednesday, February 12, 2014 2:34 PM