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Outlook Web Access on Mac OS X asking for password repeated times

Posted on 2006-05-23
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Last Modified: 2013-11-24
Hi All,

My boss (who is 8 timezones away at the moment) is having trouble with Outlook Web Access connecting to Exchange 2003.  After he logs on it continually asks for his password before it will respond to any requests.

Computer is a MacBook Pro running OS X 10.4.6, using Safari to access OWA.  Server is Windows Server 2003 running Exchange 2003 SP2.

Troubleshooting so far has been:
- reset password.
- empty Safari's cache.
- check that Internet connection is ok.  All other pages are fine.
- read through and checked items in Microsoft article "Troubleshooting Outlook Web Access logon failures in Exchange 2000 and in Exchange 2003" (KB 327843).
- checked this account from own computer from Internet (iBook, 10.3.9, Safari) without any problems.

Why is it asking for authentication again?  Any suggestions welcome!
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Question by:floogledoogle
13 Comments
 
LVL 53

Expert Comment

by:strung
ID: 16745047
Try opening the KeyChain Assistant (in the Applications:Utilities folder) and running KeyChain First Aid from the menu.

Does he have Entourage installed? He can also access OWA through Entourage and it works better than the web interface.

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Expert Comment

by:strung
ID: 16745054
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Author Comment

by:floogledoogle
ID: 16746332
Have just found out that he is having the same trouble on a PC, however there is no such problem here.  The access is apparently very erratic, with it working occasionally.  It also says that the username or password is incorrect when he enters it, though it definately is correct.

Could this be an exchange timing issue?
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Expert Comment

by:davidis99
ID: 16751460
Depending on the quality of the connection, it could very well be a timeout issue.  With a POP3 account, you'd have control over the server response (that's available through the advanced POP settings), which you could also change for an Exchange account if you were using Microsoft Outlook.  For OWA, there are no settings the user can control regarding the server response, so the Exchange Administrator would need to change the OWA timeouts.
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Author Comment

by:floogledoogle
ID: 16752616
Tested Entourage successfully with different accounts using HTTP protocol from both home and office - works quite well!  However, no such luck with the boss - Entourage reporting incorrect username or password.  Created new local user account on the Mac to avoid any Keychain problems and setup Entourage again in this, but same error.

Tried OWA in this new local user through Safari with a different user account to see if it was the Active Directory account - still same problem; it begins to load, then requests the password again, and again, and again, and eventually doesn't go any further.

Either the username/password is getting garbled, or something is timing out.
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LVL 53

Expert Comment

by:strung
ID: 16752781
Re "no luck with the boss" - do you mean you can't log in using his id and password, or he can't?
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Author Comment

by:floogledoogle
ID: 16752844
When the boss tries to log on using his username and password it fails with 'incorrect username or password', whereas I can log on with his username and password.  Checked what he was typing letter for letter - no difference.  
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Expert Comment

by:strung
ID: 16753225
This may sound really dumb, but is he sure he doesn't have capslock on?
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Expert Comment

by:strung
ID: 16753406
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Author Comment

by:floogledoogle
ID: 16758818
Checked both numlock and capslock.  Not a dumb question as I've seen it quite a few times myself!
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Expert Comment

by:ParadiseITS
ID: 16799075
This is definitively not a Mac issue, it's WIndows/Exchange -- check http://support.microsoft.com/kb/282805/en-us for more assistance with it.  

I've had this before and that KB helps fix the issue -- it's usually the IIS portion.  I think strung's suggestion ends up pointing you down this road as well.
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Author Comment

by:floogledoogle
ID: 16808140
Hi All,

Well I used RDP as a work around, but also found out that towards the end, somebody set him up with a WiFi connection at the conference centre, where OWA worked fine.  So it appears as though it had something to do with the hotel internet connection.

Thanks for all the useful and interesting comments.
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