I've tried to set up outlook anywhere using Exchange 2010 and it works well except when Outlook is first opened, the user is asked to enter their windows login password. Once it has been entered everything is fine but I need to get rid of this annoyance.

I've tested the settings on www.testexchangeconnectivity.com and everything is reported as ok. Does anyone know how I can fix this?

  • 2
    Are the users using machines that are bound to your AD? If they're not you're going to get that authentication dialog every time. – Josh Budde Aug 17 '10 at 16:06
  • Yes, the users are all in the AD and logged onto the domain. – Steve McCall Aug 19 '10 at 6:55

I managed to get this working by using NTLM authentication.

In the EMC I enabled this by going to Server Configuration ? Client Access and the properties of the mail server. Then on the outlook anywhere tab chose NTLM authentication as the method.

Then on outlook, in the account settings > more settings window > security tab I set Logon Network Security to NTLM and in the Connection tab > Exchange Proxy Settings chose NTLM authentication

And then it worked!

  • ok, so the key here is to make all of those authentication method the same: NTLM/Windows Auth on IIS, CAS wizard, and Outlook 2007 ? – Senior Systems Engineer Feb 24 '11 at 3:46

In IIS on the Exchange server, go to the Autodiscover virtual directory properties > Directory Security> Authentication Methods> Check off "Integrated Windows Authentication"

  • 1
    Not true. When logged in as a domain user and using NTLM authentication (maybe basic as well, I don't have any setups using basic auth though) the user is logged onto Outlook automatically...unless there's a problem like this. – Jason Berg Aug 17 '10 at 14:12
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    Come to think of it, I don't think I've ever seen Outlook over HTTP work without auth every time you open. – DanBig Aug 17 '10 at 14:20
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    We are using IIS on Windows 2008 R2. Windows Auth, Basic Auth and Anonymous Auth is enabled for the autodiscover VD. No change. – Steve McCall Aug 19 '10 at 6:57
  • Is there a specific way to set up NTLM auth? I'm using basic at the moment. – Steve McCall Aug 19 '10 at 6:57

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