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Cannot connect to Outlook Anywhere, Exchange 2007

Posted on 2009-05-05
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Last Modified: 2012-06-27
I have setup Outlook anywhere on our Exchange 2007 but cannot connect to it.  When I open my Outlook client, I get prompted for a password which I cannot get past.

The dialogue box states:

connect to server01.our-domain.com

Username:          ourdomain\myusername
Password:           here I enter my standard Windows / Exchange password

Now I know I am entering the correct password, but when I click ok the password dialogue box just keeps reappearing and I don't connect to Exchange, what am I doing wrong?!
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Question by:-Juddy-
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by:esmith69
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Have you run the tests at https://testexchangeconnectivity.com yet?
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by:renazonse
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I had to switch to basic authentication under the Outlook Anywhere settings. Also, goto the properties of OWA under client access in ESM and under Authentication select use forms based authentication with the user name only. Then, select the logon domain in the box at the bottom.
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by:Rajith Enchiparambil
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create a test account in ad and use it in the Microsoft test site.

https://www.testexchangeconnectivity.com/

See what it flags. Run the Autodiscover test as your problem lies with incorrect service urls.

Rajith.
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by:-Juddy-
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Thanks guys, I'll take a look in the morning and post my results.
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by:-Juddy-
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Ran the Exchange Activesync test:               All passed.
Exchange Activesync Autodiscover Test:      Failed (see attached Doc)

FYI, our web presence is called www.my-domain.com and our internal Domain is called my-domain.com.  This test reports back the IP Address of our (hosted) website.

I know this is a nightmare, but this is what I inherrited!


Attempting-AutoDiscover-and-Exch.doc
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by:esmith69
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do you have a public DNS record for autodiscover.my-domain.com configured?  This should be a regular A record, and should point to the same external IP as your Exchange server.

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by:-Juddy-
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No I don't.  Our ISP holds our MX records and public DNS info, so I need to contact them and ask for them to create an A record called:

autodiscover.my-domain.com which points to the public IP for the mail server.

Is that correct?
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by:esmith69
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Yep, that's correct.
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by:-Juddy-
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Ok I have asked our ISP to create a public A record.  Of course, this will take some time to propegate through name servers but I'll post my results once it's completed.  Thanks for your help!
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by:-Juddy-
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Ok, I now have a DNS entry for autodiscover.my-domain.com but I still have problems:

I cannot get client PC's to connect to Exchange 2007 by using Outlook Anywhere.  When I attempt to connect, I get prompted for a domain\user and password which I enter.  The box just reappears and will not connect.

When I run:  https://autodiscover.my-domain.com/autodiscover/autodiscover.xml

I get prompted for a username/password which I enter, it's ACCEPTED then I get the following displayed:

<?xml version="1.0" encoding="utf-8" ?>
- <Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
- <Response>
- <Error Time="12:15:00.4967130" Id="3584425249">
  <ErrorCode>600</ErrorCode>
  <Message>Invalid Request</Message>
  <DebugData />
  </Error>
  </Response>
  </Autodiscover>

I have had a look at the autodiscover.xml file in IIS 7 and it says it's just a placeholder.  Do I need to edit my autodiscover.xml to 'point' to my mail server?

The test PC's I have been using both run XP Pro, Outllook2007, connect to the same Exchange 2007 server.  One PC is in the domain and the one I'm testing (remotley) at the moment, isn't.
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by:esmith69
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You might want to try turning off outlook anywhere from within Exchange, then removing the rpc over HTTP windows component.  Then re-add it, and re-enable outlook anywhere in Exchange.  Sometimes this fixes wierd issues with outlook anywhere and/or the autodiscover service.
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by:-Juddy-
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This wont impact on anything else, such as Webmail (OWA)?
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by:esmith69
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It shouldn't except that it might stop/restart IIS when the rpc component gets removed and re-added.
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by:-Juddy-
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RPC is not my strong point, is there a quick way to determin that it's installed and running correctly before I go ahead and try to re-install it?
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by:esmith69
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What version of Windows server are you running?
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by:-Juddy-
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2008 Standard
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by:esmith69
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by:-Juddy-
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What have I done!!! Since installing rpc over http, client PC's connected to the domain are being asked for username / passwords!! When they enter their details, the box just reappears...I have broken Exchange, what do i do!!
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by:esmith69
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how are they entering in their username?   netbiosdomainname\username?  I would try that format.

also check the exchange server event logs, there's bound to be something in there that gives a clue what's going on.
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by:-Juddy-
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I am entering mydomain\myusername
Password
And ticking the remember my password box, still keeps cycling.  I'll check the logs now....
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by:-Juddy-
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Nothing out of the ordinary, so why does Outlook keep asking for a username and password?
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by:-Juddy-
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Just as an update, I recieve mail ok and when I click send on a newly composed mail it sends.  The password box appears when I click send/recieve, strange.
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by:esmith69
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Are all of your Outlook clients configured to use RPC over HTTP?
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by:-Juddy-
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It's happening on 2 clients so far and neither are configured to use RPC over HTTP.
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by:esmith69
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what happens if you launch their Outlook using the /rpcdiag switch?
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by:-Juddy-
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Right, it seems to have stopped.  I have disabled Outlook Anywhere and run Ipconfig /flushdns then /registerdns.  Not sure which bit solved the problem, but the password box was appearing every 30 seconds or so, it's been 5 minutes now and neither PC is being prompted for a username / password.
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by:-Juddy-
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Spoke too soon, password box is back...just running the diags now...
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by:-Juddy-
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It connects to everything ok, then the password box reappears.  I reauthenticate, click Reconnect, it connects then the password box reappears!
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by:esmith69
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the outlook clients are not using rpc over HTTP, but are they using cached exchange mode?
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by:-Juddy-
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Correct.
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by:esmith69
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Have you tried creating a new Outlook profile for them?
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by:LANm0nk3y
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by:-Juddy-
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I haven't, what's the best way to do that?
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by:esmith69
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Just go into the control panel, then to the mail icon.  Do "profiles", then "add", then follow the steps to add in the required info.  Make sure to choose that profile the next time you load Outlook.
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by:-Juddy-
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I was expecting some kind of fancy trickery!!  Yes, I've just removed my old profile and re-added it, it's just downloading a local copy of my mailbox now.....whilst it's doing that, do you happen to know if I need a DNS entry for autodiscover.my-domain.com that point to both my internal and external IP addresses for the mail server?
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by:esmith69
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on your internal DNS you'll need it to point to the internal IP of the mail server

on your external DNS it will need to point to the external IP
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by:-Juddy-
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It's just finished downloading my profile and it asked for a user/name password again.
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by:-Juddy-
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That's what I thought.  I have a local DNS record on our domain controller which points to the internal IP address of the mail server, and our ISP has today created a new public DNS record for the external address, which should be propegating though their DNS servers as we speak.
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by:-Juddy-
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The box is popping up every 20 seconds or so now!!
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by:esmith69
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Do you have any other email accounts configured in the Outlook profile?  Like maybe a POP account or something?
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by:-Juddy-
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No, just my Exchange account.
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by:esmith69
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And you're running Outlook 2007?
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by:-Juddy-
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I am.  If I click cancel on the password request, it says 'needs password' in the bottom right corner.  If I send a mail, it goes and my connection re-establishes; this is the same for recieving mail.  It seems I can send and recieve ok, it just keeps asking for a password!!
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by:esmith69
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by:-Juddy-
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I added the registry hack as descrived, rebooted for good measure still getting the prompt.  Ever since I installed RPC over HTTP this popup keeps appearing.  it has happened to 2 other client PC's now as well.
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by:esmith69
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If you go into the properties for the Exchange account (within the Outlook profile), then go to the "Security" tab, what does it have selected under "logon network security"?
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by:-Juddy-
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Negotiate Authentication.  I am logged into Outlook over a VPN connection and so far, no password prompts.
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by:-Juddy-
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But when I start outlook /rpcdiag every thing connects, but the same of prompt for username password keeps appearing.
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by:esmith69
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try changing that to NTLM and then restarting outlook.  it may prompt once per Outlook session, but then it shouldn't continue to pop up

Another thing you might consider is trying to enter in the username/password info in a slightly different format from whatever you're using right now.  I know I said earleir to use netbios\username, but sometimes you have to just use the username.
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by:-Juddy-
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Chnaged to NTLM and have tried the following combos:

domain\user
servername\user
server.domain\user
user

All result in the same thing, the password box just keeps appearing.  This is obviously down to me installing RPC over HTTP can I diabable something to test this out?
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by:esmith69
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On your Exchange server, run the Test-MapiConnectivity test.  

http://technet.microsoft.com/en-us/library/bb123681.aspx
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by:-Juddy-
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Blimey!! Which one of those three do I use and do I have to adjust any of the code?
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esmith69 earned 250 total points
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Sorry, ignore that last post about the test-mapi thing.

Did you try changing the authentication method in the Outlook profile to Basic?  I know you said originally it was set to negotiate and that changing it to NTLM didn't help at all.
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by:-Juddy-
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I did.  I'm going to award you the points for a first class effort, but I have uninstalled RPC over HTTP on the mail server as it's causing far too problematic.  I may re-visit it in the future, but for now it's causing too many headaches.  Many thanks for your help!
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by:pc-cyt
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If outlook 2007 isn't remembering its password for an exchange account (non domain member) then try in outlook  accounts > your profile > repair... (on toolbar)  

My outlook 2007 using outlook anywhere only asks once on program start for usr/pwd

Hope this helps someone.
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