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Outlook users continually prompted for password when trying to login

Posted on 2011-09-26
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Last Modified: 2012-05-12
Hello,

I have searched and read dozens of articles but haven't seen anything that specifically matches my case.

I have two sites, chicago and ohio.  Each site has a exchange 2010 server, and users are on outlook 2007 or 2010.  Three weeks ago, the ohio team needed an external IP and port 443 for it.  They intentionally borrowed the one used for the exchange server.  Two hours later a different external IP and port 443 for it was freed up.  Since that moment of changing the IP, 4 users out of 30 in ohio have had trouble connecting to the server with their outlook clients.  OWA and email on phones has not been affected.

The trouble that they have had is outlook keeps prompting these 4 users for username/password.  We do have outlook anywhere enabled, and autodiscovery for 2010 almost always tries to use that, but switching users to OO or not to use OO doesn't appear to make a difference, the password popup keeps appearing.  I have tried creating a new profile, but that doesn't seem to be a permanent fix.  All 4 users have laptops and have tried this from home, it seems to be worse when trying to login at home.  Those who use OO get the popup, so I had them connect via a PPTP vpn, same problem, so I had them connect with a SSL vpn, same problem.  One recent change I made was to move the firewall policy for exchange higher in the order list, in hopes that it made a difference.

Any ideas?  I am 90% sure that changing the IP/port did this?   users say thats when they last got an email.  I deployed a new laptop to one user and that fixed it, so far.  Do I need to delete a whole windows profile?
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Question by:inferno521
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by:dexIT
ID: 36600068
They may need assistance connecting using the correct login format. I've had users in the past attempt to connect using local\user opposed to domain\user. Have you attempted to log in from another source?
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by:inferno521
ID: 36600105
dexIT:
using domain\user and user@domain.com or user@domain.local doesn't help.  I'm not sure what you mean by login from another source.  But OWA has never failed for these users, neither has their phones.   They have taken their laptops home, and still have these errors, and have used Time Warner wifi hot spot devices, and still experience this error.
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Author Comment

by:inferno521
ID: 36717046
Ok so I enabled logging and here's what I get:



2011/09/28 08:21:14.242: Request to URL: https://email2010.mydomain.com/ews/exchange.asmx

2011/09/28 08:21:14.242: Request action: http://schemas.microsoft.com/exchange/services/2006/messages/GetUserOofSettings

2011/09/28 08:21:14.242: Request XML: <?xml version="1.0"?>

<q:Envelope xmlns:q="http://schemas.xmlsoap.org/soap/envelope/"><q:Body><ex12m:GetUserOofSettingsRequest xmlns:ex12m="http://schemas.microsoft.com/exchange/services/2006/messages"><ex12t:Mailbox xmlns:ex12t="http://schemas.microsoft.com/exchange/services/2006/types"><ex12t:Address>myuser@mydomain.com</ex12t:Address><ex12t:RoutingType>SMTP</ex12t:RoutingType></ex12t:Mailbox></ex12m:GetUserOofSettingsRequest></q:Body></q:Envelope>

2011/09/28 08:21:14.242: Sending request

2011/09/28 08:21:14.694: Request sent

2011/09/28 08:21:14.694: Response error code: 00000000

2011/09/28 08:21:14.694: HTTP status code: 500

2011/09/28 08:21:14.694: -------------------------------

2011/09/28 08:21:14.694: There is an error in request/response.

2011/09/28 08:21:14.694: XML response:<?xml version="1.0" encoding="utf-8"?><s:Envelope xmlns:s="http://schemas.xmlsoap.org/soap/envelope/"><s:Body><s:Fault><faultcode xmlns:a="http://schemas.microsoft.com/exchange/services/2006/types">a:-2146233088</faultcode><faultstring xml:lang="en-US">The user and the mailbox are in different Active Directory sites.</faultstring><detail><m:ErrorCode xmlns:m="http://schemas.microsoft.com/exchange/services/2006/messages">-2146233088</m:ErrorCode></detail></s:Fault></s:Body></s:Envelope>

2011/09/28 08:21:14.694: -------------------------------



email2010 is the main exchange server, her mailbox is on email2, so I believe that is the problem.  Is this an autodiscover problem?
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inferno521 earned 0 total points
ID: 36916919
The problem was something was cached on the computers in that office.  Computers not in that office didn't have that computer.  So when I shipped three laptops there, they didn't have that problem.  Eventually this either went away on its own or some combination of flushing the cache and deleting and recreating host a records on dns fixed this.
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Author Closing Comment

by:inferno521
ID: 36941152
I'm not 100% that this fixed the problem, but the problem is fixed
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