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Outlook 2007 keeps prompting to authenticate to old hosted exchange server after migration

Posted on 2008-10-20
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Last Modified: 2012-05-05
We have recently migrated from 1 hosted exchange server solution to another and are experiencing multiple secondary login dialogs referencing the old hosted exchange server.  We are using Outlook2007 with RPC over HTTPS and it is working fine, however the secondary dialogs are becomig quite annoying.

The new provider says they have never seen this before, when using their Outlook Profile Helper Migration tool.  Is it possible that the registry needs to be cleaned up on these machines or a file is stll being called that has old exchanger server info?
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Question by:jthoren
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Expert Comment

by:Probity
ID: 22763927
Check each machine's password cache -- which can be accessed via

Start -> Run
control userpasswords2

Click the advanced tab, then click Manage Passwords

Remove all the old saved passwords (and even the new ones) and then reopen outlook.  Should prompt you for credentials once, then save them.

Let me know if it works.
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Expert Comment

by:Exchange_Geek
ID: 22765940
If you are re-configuring OL profile and still facing same issue - type

control keymgr.dll upon start-run and remove all old stored user name and passwords
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Author Comment

by:jthoren
ID: 22768634
I have tried both items and it appears they go to the same place.  I removed all passwords and then opened Outlook.  I logged into the new exchange server successfully and the received 4 login  prompts over a period of approx 5 min to the old server.  Anybody have any more ideas?
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Expert Comment

by:Probity
ID: 22772355
Now go back into the userpasswords2 manage passwords screen and ADD the new credentials for each user, then reopen outlook.  Should solve it.

However, my company provides a Hosted Exchange 2007 solution and we had to put several entries in each PC's saved passwords (for different servers on our end).  

I overcame the tedium by writing a custom app to add the entries with the user only entering their info once.
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Expert Comment

by:Probity
ID: 22772358
P.S. take note of the exact name of the server listed at each logon prompt... again, for my organization its:

webmail.domain.com
autodiscover.domain.com
cassrv.domain.local

all of which need to be added to the saved passwords in order for prompting not to happen
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Author Comment

by:jthoren
ID: 22772442
Thank you Probity, will this really resolve the issue with Outlook trying to authenticate to the old hosted exchange server?  We are not wanting Outlook to look for the old server at all is the issue we are resolving.  The secondary login is becoming an annoyance and the lower right hand corner of outlook 2007 keeps saying it needs a password.

Let me know if I completely missed something, I appreciate the help.
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Expert Comment

by:Probity
ID: 22772488
Well ideally you would create a new profile for each user... its very difficult to get it to swap servers in the same profile -- but the managed passwords is the next best bet
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Author Comment

by:jthoren
ID: 22772721
In looking a bit deeper the utility that the exchange provider provided us actually creates a new profile and redirects Outlook to use it.  Separate OST file and NK2 files as well, it is pretty strange that is sure.  For whatever reason outlook is gloming onto the old server name even though it is not being referenced in the Outlook settings.

JT
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Expert Comment

by:Probity
ID: 22772740
And just to clarify, you've removed everything from your managed passwords list?
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Expert Comment

by:Probity
ID: 22772742
Also, would you mind if i ask who your provider is?
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Author Comment

by:jthoren
ID: 22772750
Correct.  We used 1and1.com and went to intermedia.net, due to SLA not being delivered upon.
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Expert Comment

by:Probity
ID: 22772794
And I assume you've gone over all the exchange RPC settings, http:// and the mutual authentication SSL and all that is the new server?

Which server addresses are prompting you for passwords?
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Author Comment

by:jthoren
ID: 22773641
Yes,  the server login that comes up is from the former server or 1and1.com's login box.  All RCP settings only reference the new server too.  Very odd behavior.

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Expert Comment

by:Probity
ID: 22779436
New profiles are probably going to be your only option then
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Author Comment

by:jthoren
ID: 22779666
You mean create new windows profiles for the users?

JT
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Accepted Solution

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Probity earned 500 total points
ID: 22781871
new outlook profiles

Control Panel -> Mail -> Profiles
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Author Comment

by:jthoren
ID: 22800745
We had tried this already.  We have even gone as far as deleting them all and recreating a new one and the issue still comes back with the secondary login.


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LVL 33

Expert Comment

by:Exchange_Geek
ID: 22802660
Ok let us hit this issue on the head - do you mind increasing OutLook logging and take a wireshark trace (this is similar to network monitor used by Microsoft ). -please perform the above steps at the time when the issue happens (else reading wire shark trace would take ages if you keep it on for entire day)

I am sorry i have not read each and every entry (to be honest) on this thread.

Also, are you hosting your own server - or is it with some one else keeping your mailbox and your paying for it ?? If it is you i can quickly ask you questions to troubleshoot the issue.

Also, ( i know it is a bit bugging) but please do tell me how many users are affected and how many NOT affected - which versions are each one using (if provided with OL version + SP applied) along with combination of work station O/S would help. Thanks.
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Author Comment

by:jthoren
ID: 22808194
I will check this tomorrow and working on getting a trace.

Thank you

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Expert Comment

by:pc3000
ID: 25926007
There's a registry key that points to an XML file that makes the computer initiate an autodiscover request for the old exchange server. Delete the key and the prompt goes away.
http://nuage-it.com/blog/?tag=prompting-for-old-exchange-password
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