Agree with removing the older password in Credential Manager for prior version 
of Outlook.

Alice

From: listsad...@lists.myitforum.com [mailto:listsad...@lists.myitforum.com] On 
Behalf Of Hugo Hernandez
Sent: Wednesday, December 13, 2017 3:11 PM
To: exchange@lists.myitforum.com
Subject: [SPAM] [Exchange] RE: Outlook 2016 prompt for password connecting to 
Exchange 2010
Importance: Low

Are the users changing their password either before or after the upgrade?  I've 
only noticed this issue when a user changes their password and Windows doesn't 
update the cached password in their vault.  Deleting the cached password 
usually does the trick.

Hugo Hernandez
Network Administrator

Insteon
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From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Maglinger, Paul
Sent: Wednesday, December 13, 2017 1:32 PM
To: 'exchange@lists.myitforum.com'
Subject: [Exchange] Outlook 2016 prompt for password connecting to Exchange 2010

I seeing issues where users that have been upgraded from Outlook 2010 to 
Outlook 2016 are getting prompted for credentials when attempted to connect to 
the Exchange 2010 server.  After entering username and password Outlook comes 
up fine.  Looking at the Outlook Connection Status it's getting hung up when 
connecting to one of the mailbox servers (in a DAG) for the Exchange Public 
Folders.    It doesn't happen on a consistent basis.  Sometimes they get 
connected without a hitch.  The CAS/HUB servers are set up as a CAA using 
Windows NLB.

I did some Googling and found references similar but it mostly involved 
occurring after migrations from Exchange 2010 to Exchange 2013.  The most 
common resolution involved going into IIS and changing the authentication 
settings for EWS and Autodiscover each to disable Anonymous Authentication and 
then under the Advanced Settings for Windows Authentication, enable Kernel-mode 
authentication.  Then restart IIS.  I couldn't find anything specific about 
problems after upgrading from Outlook 2010 to Outlook 2016 and connecting to 
Exchange 2010.

Besides the prompting everything is working fine and worked fine with the old 
Outlook.  I'm looking for a bit of understanding why this started happening and 
the feasibility of the above suggestion correcting the problem.  One concern is 
disabling the Anonymous Authentication.  The other is that apparently the 
Kernel-mode authentication is enabled by default - which tells me someone 
disabled it.  I'm not sure why someone would have done that other than a 
reference I found where sometimes Kerberos authentication fails when you have 
kernel mode authentication enabled.

Does someone have a possible explaination?

Paul

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