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Autodiscover and Outlook Anywhere not working at all

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  • Autodiscover and Outlook Anywhere not working at all

    Recently installed a new 2008 R2 server with Exchange 2007 on it, migrated mailboxes from an Exchange 2003 server, which is still online.

    Steps I've done so far...
    1) Created a DNS record for to IP "X"
    2) Ports 80 and 443 coming inbound on IP "X" gets NaT'd to my internal server
    3) I have set the Internal and External URLS to be the same,
    4) There is a UC cert applied that covers: yha2.domain.local, yha2,,

    1) Browsing to asks for a password, if you type in the credentials you receive a runtime error.
    2) Adding a new mailbox to a non-domain joined client, type in mailbox name and password, retrieves settings, asks for the credentials for connecting to the account, but then says it is has setup the account as IMAP instead of exchange.
    3) Already setup Outlook profiles, that are on domain joined computers, are asking for credentials each time they open Outlook
    4) Using testexchangeconnectivity, Autodiscover and Outlook Anywhere both pass with no red marks.

    Results from "get-webservicesvirtualdirectory:

    InternalNLBBypassUrl : https: //yha2.domain.local/ews/exchange.asmx
    Name : EWS (Default Web Site)
    InternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
    ExternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
    BasicAuthentication : True
    DigestAuthentication : False
    WindowsAuthentication : True
    MetabasePath : IIS://YHA2.domain.local/W3SVC/1/ROOT/EWS
    Path : C:\Program Files\Microsoft\Exchange Server\Clie
    Server : YHA2
    InternalUrl : https: //
    ExternalUrl : https: //
    AdminDisplayName :
    ExchangeVersion : 0.1 (8.0.535.0)
    DistinguishedName : CN=EWS (Default Web Site),CN=HTTP,CN=Protocols,
    CN=YHA2,CN=Servers,CN=Exchange Administrative G
    roup (FYDIBOHF23SPDLT),CN=Administrative Groups
    ,CN=Yavneh,CN=Microsoft Exchange,CN=Services,CN
    Identity : YHA2\EWS (Default Web Site)
    Guid : 8dcabd46-05eb-46ea-8c95-4d8c7b4d6085
    ObjectCategory : domain.local/Configuration/Schema/ms-Exch-Web-Services-Virtual-Directory
    ObjectClass : {top, msExchVirtualDirectory, msExchWebServices
    WhenChanged : 4/27/2011 11:36:22 PM
    WhenCreated : 4/11/2011 2:58:54 PM
    OriginatingServer : YHADC1.domain.local
    IsValid : True

    Any help would be greatly appreciated. This has been trying my patience and after reading articles after articles, it doesn't seem like I am getting anywhere.

  • #2
    Re: Autodiscover and Outlook Anywhere not working at all

    Have you done all the updates? We had a network a year ago with these kinds of problems. If the client Office had been updated it wouldn't work properly with Exchange unless we reinstalled it and turned off updates to Office.

    Eventually after several months one of the update rollups for Exchange fixed the problem although we weren't offered the rollup through Microsoft updates and had to download it manually.


    • #3
      Re: Autodiscover and Outlook Anywhere not working at all

      First this does not seem like an Autodiscover problem because of how Outlook acts after you open it ... ie asking for credentials. Just to confirm ... what happens when you remove a PC from the domain, and re-add it manually, then delete the Outlook profile and then manually create one? Do you still get prompts for password?


      • #4
        Re: Autodiscover and Outlook Anywhere not working at all

        Actually is can be an autodiscover related problem. We our client was having the problem you could see the source by running outlook /rpcdiag. This showed that it was the autodiscover request that was resulting in a password prompt and not the exchange connection,