Outlook password prompt for mailboxes on Exchange 2013 CU1

I migrated a few users from our Exchange 2007 SP3 Update 10 server to Exchange 2013 CU1. Now in Outlook they are getting a password prompt, and it won't accept their password. Our public folders are still on Exchange 2007 if that makes a difference.
I tried running
Test-OutlookConnectivity -GetDefaultsFromAutoDiscover:$true
but it says it doesn't recognize the parameter -GetDefaultsFromAutoDiscover:$true
Here's the values for Get-OutlookAnywhere:
ExternalHostname : legacy.domain.com
InternalHostname :
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods : {Ntlm}
ExternalHostname : mail.domain.com
InternalHostname : clippers.domain.local
ExternalClientAuthenticationMethod : Negotiate
InternalClientAuthenticationMethod : Negotiate
IISAuthenticationMethods : {Negotiate}

Hi GraffitiK
How is your test? Did the issue resolve?
Cheers
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Zi Feng
TechNet Community Support

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I am in the process of a 2010 to 2013 migration. The only issue I can't seem to manage is an authentication issue with Outlook 2010. My Outlook profile consists of my Exchange 2013 mailbox and a shared mailbox on Exchange 2010. Initially, Outlook was prompting
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Hi Dennis,
Please open Outlook - press CTRL key - right click on the Outlook icon from right bottom corner taskbar –Connection Status to check the connection for your Exchange 2010 mailbox with shared 2013 mailbox. The following example in my test results:
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In Outlook side, please ensure the following settings in Account Settings:
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Outlook Password prompt for Linked Mailboxes from certain Domain

Hello,
As part of a migration project, I'm trying to connect Outlook with Linked Mailboxes from users in a trusted domain.
I'm able to create the linked mailbox on the Exchange 2013 (CU7) server without any issue, but when I try to configure Outlook for these mailboxes, it is prompting for credentials permanently and won't start. Log on to OWA with the same user from the trusted
domain is working fine.
I'm able to configure Linked mailboxes from another trusted domain without any problems.
I've already recreated the trust between these two domains (validation tells everything is ok)
DNS is configured with conditional forwarders in both domains and name resolution looks ok to me (ping and nslookup)
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Infos:
DomainA: Domainlevel 2012 - Exchange 2013 - Forest trust to Domain B and C
DomainB: Domainlevel 2008 - Exchange 2010 - Forest trust to Domain A - Outlook for linked Mailboxes of DomainA works fine
DomainC: Domainlevel 2008 - Forest trust to Domain A --> can't connect Outlook to LinkedMailboxes of this domain.
Is there anything else I can check?

Hi,
Please check whether the server is configured to only accept NTLM version 2 and reject NTLM and LM, and the Outlook client computer is not configured with the same LAN Mananger authentication level.
Check DC, Start -> Programs -> Administrative Tools -> Security Options -> Note the LAN Manager authentication level.
Check DC's policies, Start -> Programs -> Administrative Tools -> expand Security Settings\Local Policies -> Security Options -> Note the Lan Manager authentication level.
IMPORTANT： You may also have to check policies that are linked at the site/domain/organizational unit levels to determine where the LAN Manager authentication level must be configured. Configure the LAN Manager authentication level to "Send
NTLMv2 response only". If you want to implement NTLM version 2 in your network, make sure that all computers in the domain are set to use this authentication level.
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Hi
In your testing creating bulk mailboxes alone will not help . We need to populate some data's in the databases so that the databases are written with some values and they contain some data.
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First you need to create few number of mailboxes.
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Outlook 2010 prompting for password each login to Exchange 2013

We have a new member server w/ Windows Server 2012 and Exchange 2013. User's mailboxes were migrated from an old Windows Server 2003 server w/ Exchange 2003 by creating new empty mailboxes in Exchange 2013 then we exported/imported
.pst files instead of migrating exchange stores. Every time any users opens Outlook, they are being prompted to log in with domain credentials. Obviously I'm clicking on "Remember my password", too. The workstations are all
using Outlook 2010 and on a mix of Windows XP SP3, Windows 7 SP1 and Windows Server 2008 R2 (terminal server with Outlook 2010 installed for remote users). Some users were using Outlook 2010 prior to the migration to Exchange 2013 and some were on Outlook
2007 but upgraded to Outlook 2010. I'm almost to the point of telling the users it's a new "feature" of Exchange 2013. I'm confident that it's not stored passwords or credentials on the workstations, I've removed, deleted, created and
recreated those credentials. I've changed domain passwords and that didn't help either. Any hints, tips or suggestions would be greatly appreciated.

Hi
These settings can be found under your Outlook profile, "More Settings > Connection > Exchange Proxy Settings."
If you have Outlook Anywhere enabled, then you should force all Outlook clients to use HTTP when connecting. Ensure you have "On fast networks, connect using HTTP..." AND "On slow networks, connect using HTTP...". If you
don't, anytime you dock, undock, get a new IP address, refresh your IP address, go to sleep, idle, anything that causes your IP stack wants to renegotiate connective will cause a password prompt to appear, EVERYTIME.
Terence Yu
TechNet Community Support

Why does Outlook keep prompting for password

We have seen our community members ask questions about Outlook keeps prompting for credentials many times. This issue could be caused by numerous reasons. Below is a list of the most common reasons for this problem:
Outlook is configured to prompt you for credentials
Incorrect password cached in credential storage
Required Authentication Settings for outgoing server and incoming server
Outlook Anywhere is not configured to use NTLM Authentication
Corrupt Outlook profile
Slow or unstable network connection
Antivirus programs
Shared calendars
Outlook is configured to prompt you for credentials
If you are using an Exchange account, there is a setting in your Outlook profile to always prompt for logon credentials. To find the setting, please follow:
1. In Outlook 213, go to File tab > Info >
Account Settings > Account Settings…
2. Highlight your Exchange account and click Change button.
3. Click on More Settings button.
4. Select the Security tab.
5. Under the User Identification, make sure the “Always prompt for logon credentials” option is not selected.
If you are using other types of email, please make sure you have ticked the option “Remember password”.
Incorrect credential cached in Credential Manager
Your Windows system stores user credentials on your computer. If the cached credentials are incorrect, you will be prompted for password. This issue usually happens after the password for your domain user account is changed. Before your password changed,
you saved your credentials. The stored credentials are not overwritten when Outlook triggers the authentication prompt even if you enable the Remember my credentials option.
To fix this issue, you need to remove the corrupted credentials, follow these steps:
Click Start, click Control Panel, and then click Credential Manager.
Note If View by is set to Category, click User Accounts first, and then click Credential Manager.
Locate the set of credentials that has Outlook in the name.
Click the name to expand the set of credentials, and then click Remove from Vault.
Repeat step 3 for any additional sets of credentials that have the word Outlook in the name.
Required Authentication Settings for outgoing server and incoming server
Different email provider may need different authentication settings. Please make sure you have set the server settings correctly. You can contact your email provider to gather the information.
In general, we select the “My outgoing server (SMTP) requires authentication” option and the first bullet “Use same settings as my incoming mail server”.
In addition, click on the Advanced tab and check if you have enter the correct Server Port Number and select the correct encrypt type. Below is a screenshot for an IMAP account:
Outlook Anywhere is not configured to use NTLM Authentication
The Outlook Anywhere feature allows you to access your Exchange account remotely from the Internet when you are working outside your organization's firewall.
When using Outlook Anywhere to connect to your Exchange server, we need to choose
the authentication method among Basic Authentication, NTLM Authentication and Negotiate Authentication. The difference among them is the way that the passwords are sent when connecting to the server. With Basic Authentication,
the password is sent in clear text. Using NTLM Authenticationcan significantly reduce the number of password prompts.
To check the authentication setting, please go to File > Account Settings > Account Settings,
select the Exchange account, and then click
Change. In the Change Account wizard, click
More Settings, and then click the Connection tab. Click the Exchange Proxy Settings button and now, you can see the settings under
Proxy authentication settings. Try to change the authentication to
NTLM Authentication and then check the issue again.
Slow or unstable network connection
If your network connection is slow or unstable, Outlook may lose connection to the mail server. When Outlook try to reconnect, it will prompt for the credentials. To verify this, please switch to a stable network environment and then check if this issue
persists.
Corrupt Outlook Profile
Corrupt profile may cause Outlook to no longer remember your password. Please try to create a new mail profile in Control Panel and reconfigure your email account in the new profile to fix the issue. To create a new mail profile, you can refer:
http://support.microsoft.com/kb/829918
Antivirus software
Antivirus software usually integrates into your Outlook and it may cause some conflicts. Try to temporarily turn off your antivirus software to check if the issue will be gone.
Shared Calendar
Shared calendars can impact the user credentials, this issue may also occur if you have shared calendars opened in Outlook. You can try to unselect the shared calendar to check the result. It’s recommended to not open the shared calendar unless you want
to view them.
If you have any comments, welcome to post in the forum. Thank you.
Please click to vote if the post helps you. This can be beneficial to other community members reading the thread.

Nope...
I went through point by point by point, top to bottom, checking and verifying every single item as a possible cause for why my system (Outlook 2013 running on Windows 8.1 and connecting to Exchange 2010) insists on prompting me for my password every single
time I start Outlook. None of the solutions worked, my system still prompts me. I don't even have to supply a password. When the prompt dialog appears, I just cancel it. Within a few seconds, the bottom Outlook status bar changes to
"Need Password" with a key icon to the left. Then I just click on that message and immediately Outlook connects to Exchange.
The freaking software is BROKEN! Period.

Micrsoft Outlook somtimes prompting for username and password

hello All ,
I Have Exchange 2010 sp3 installed two mailbox servers & two HUB & CAS Servers and Outlook sometimes prompting for username and password .
how can fix it .
Thank you

Hi,
Please check the following points:
1. Does the issue happen to your external users or internal users?
2. For all users or some specific users?
If the issue happens to internal users, please configure the authentication in Outlook Security tab with Negotiate Authentication to have a try.
Thanks,
Winnie Liang
TechNet Community Support

Internally installed Outlook 2010 prompts for password using external smtp email as user id

Hi,
After exchange 2007 to exchange 2013 migration all internally connected outlooks 2010 (xp, vista, win7, win8) prompt for password using external email user address as user id.
Below some of my settings and informations.
Internal domain: contoso.local
External domain: contoso.com
Exchange is NOT published to Internet at all.
Internally OWA, ECP runs OK.
Test-OutlookWebservices with user.name(at)contoso.local or contoso\user.name - runs OK
Test-OutlookWebservices with user.name(at)contoso.com - fails
Common scenario - (all happens internally):
1.User starts Outlook
2.Outlook prompts for password with default user.name(at)contoso.com as id
- while user tries to authenticate using his domain password - outlook re-prompts
- while user changes id from user.name(at)contoso.com to user.name(at)contoso.local or contoso\user.name and authenticates - Outlook connets to exchange and till next Outlook it runs ok.
I am bus with that issue since 1 week and I am already bit tired. I was looking for answer via gogle/bing and went through tons of "Outlook perpetually prompts for password" threads and blogs. No success.
Do you have any clue where else start to play with that?

Hi,
Thank you for answer - no luck
>NExt og to Connection tab - Exchange Proxy settings - Proxy authentication settings - is it set
>to NTLM or Basic?Give it a try on one of them.(if set to NTLM change to basic and vise versa).
On both settings the same results - Outlook is prompting for password.
>Another thing you could try is og to Internet Explorer - tool -internet options- Security - click local
>intranet - >custom Level and scroll Down to bottom and put check mark on automaticly logon
>With current username >and password.
>Do this on Trusted sites as well,if Your domain is listed under trusted sites
The same results - Outlook isprompting for password.
Should not be some kind of mapping set somehow in AD between user.name(at)contoso.com and user.name(at)contoso.local?
I have impresion that issue is somewhere in the fact that outlook is trying to connect using contoso.com instead of contoso.local in ntlm credentials.

Outlook 2010 clients cannot access their Online Archive mailbox in Exchange 2013??

Hello,
I have an issue where my Outlook 2010user cannot see/access their Archive mailbox when they are migrated from Exchange 2010 to Exchange 2013.
Both the live and archive mailbox is in Exchange 2013, the user can launch Outlook but if they click on their Archive mailbox it is unavailable.
Once the user is upgraded to SP2 or Outlook 2013 they have no issues accessing their archive mailbox.
These users have the minimum required Outlook version (14.0.6126.5000),
they are running 14.0.6129.5000.
Is there a different requirement on the Outlook client if the user has an archive mailbox in Exchange 2013 as well?
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Hi,
Is there any update on this thread?
Thanks,
Please remember to mark the replies as answers if they help and unmark them if they provide no help. If
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Simon Wu
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Outlook 2007 - single profile connecting to Exchange 2013 / 2007 mailboxes

Hi,
I am in the early part of a migration from Exchange 2007 to Exchange 2013. So far I have 2013 installed and running in a DAG and just moved my own mailbox to the new server.
I set up a new profile in Outlook 2007 which connects to my mailbox on Exchange 2013. The problem is that I need to add additional mailboxes to my profile which are still hosted on Exchange 2007, however this is not working.
I thought at one stage I tested this and was able to get it work with a test mailbox also hosted on Exchange 2013.. but maybe I never did.
Does anyone know if this is possible at all (single Outlook profile, primary mailbox hosted on Exchange 2013 and other mailboxes on Exchange 2007). Most of our users have an additional mailbox mapped in their profile so I hope there is some way around this.
Thank you!

Hi,
It is possible to open a shared mailboxes on a legacy server.
Your problem could be caused by:
Not having one of the later CU installed (read CU4 or CU5)
Incorrect authentication methods configured (see link below)
Outlook is not at the latest patch level
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http://support.microsoft.com/kb/2834139
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Outlook Authentication prompt after migrating from 2007/2013

I have a very simple environment. 3 new Exchange 2013 servers in a DAG behind a load balancer. Most users are still on Exchange 2007 environment. Autodiscover has been configured for load balanced name. There is no External Outlook
Anywhere connectivity. I have NOT enabled Outlook Anywhere in the 2007 environment. I have a simple Lync 2013 environment. 1 Server in a standard pool with no external connectivity. I have integration with OWA 2013 and Lync working.
All versions of Outlook are at least on the patch level required for Exchange 2013.
My issue is random password prompts in Outlook for some (not all) users with mailboxes on Exchange 2013. This password prompt appears to be coming from the load balanced Outlook anywhere name. I have had a few reports of users on Exchange 2007
getting an error stating they cannot open default set of folders. If I have them exit Lync 2013 client and open Outlook again it works fine. They can then open Lync without issue. Closing and opening Outlook will no longer reproduce the issue.
It seems like Lync is causing an issue here somewhere, but I have no idea where.
Lync BPA completes without any warning or errors. All test cmdlets complete without any errors.
2013 Outlook Anywhere settings:
Name                               : Rpc (Default Web Site)
ExternalHostname                   :
InternalHostname                   : mail.company.com
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}
Get-AutodiscoverVirtualDirectory|select *auth*
InternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
ExternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
LiveIdNegotiateAuthentication : False
WSSecurityAuthentication      : True
LiveIdBasicAuthentication     : False
BasicAuthentication           : True
DigestAuthentication          : False
WindowsAuthentication         : True
OAuthAuthentication           : True
AdfsAuthentication            : False
brian smith

I just could not let this go last night. The issue was occurring when I moved a mailbox to 2013.
2 scenarios
#1. Users mailbox moved from 2007 to 2013. Profile has a secondary mailbox that is still on 2007. When entering Outlook they are prompted for
a password into the internally resolvable load balanced name (mail.company.com). If I remove this secondary 2007 mailbox they work fine, UNTIL they try to access anything on 2007 (calendar, Public Folder, another mailbox, etc). When they do attempt they
are prompted for a password.
I have seemingly fixed this error by adding the external URL back to AutoDiscover on 2013 based on
http://support.microsoft.com/kb/2839517<u5:p></u5:p>. Even though we have no intentions of using Outlook Anywhere externally.
During this troubleshooting I also changed InternalClientsRequireSsl from false to true. Now I have clients reporting errors in their event log “A fatal error occurred while
creating an SSL client credential. The internal error state is 10013." I do not think changing this to require SSL, but I’m almost scared to change it because this issue
is seemingly resolved.
#2 mailbox that is only accessed as a shared mailbox Mailbox is moved from 2007 to 2013. Users attaching to the mailbox are still on 2007. This works perfectly fine for some. However others receive a password prompt each time they open Outlook.
If the 2013 mailbox is removed from their outlook profile they receive no prompt. If I manually remove the mailbox from their profile and add it back the prompts go away. I have not been tracking client versions, but these last 4 are running 12.0.6691.5000.
I also noticed in checking the connection status all 2007 references are using [Nego] for authentication and mail.company.com is using NTLM. Is this normal? This is the same in my test environment, but I can’t replicate this issue in my test environment
either.
I’m very stumped.
2013 Outlook anywhere config:
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}
SSLOffloading                      : True
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : True
2007 Outlook anywhere config:
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm}
SSLOffloading                      : True
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : False
brian smith

Outlook Password Prompts events

Few mailboxes (not many) where reported with outlook password prompt and I'm trying find events related to outlook password prompts..
Need help on, where to find the event logs related to outlook password prompt.. Do I need to configure any perform or new captures to captures those events ?

Hi,
I'n my experience this can be cause by additional mailboxes mapped to the account.
On the client that is experience the password prompt, right click on the Outlook icon in the bottom right while holding shift. Then select Connection status. You should be able to see the connections to the exchange.
Check is there is any connection that is in the state connecting when you get the password prompt. The Type will tell you what kind of connection this is and if it's an additional mailbox or mapping.
When a user has full permissions to an mailbox it is automatically mapped to the user.
You can disable this if wanted.
http://technet.microsoft.com/en-us/library/hh529943(v=exchg.141).aspx
or simply edit the attribute on the users account
\Mattias
http//blog.gsec.se

Cannot disable a mailbox in Exchange 2013 CU6!?!?!?!

I cannot disable a mailbox in Exchange 2013 CU6. I get the following error:
Anyone seen this error? As you know, I just want to remove the Exchange attributes from the user object in Active Directory. Of course, deleting the user object works just fine but don't want to go that route.

I tried with the EMS (Powershell) and I still get an error:
[PS] C:\>disable-mailbox [email protected]
Confirm
Are you sure you want to perform this action?
Disabling mailbox "[email protected]" will remove the Exchange properties from the Active Directory user object and mark the mailbox in the database for removal. If the mailbox has an archive or remote archive, the archive will also
be
marked for removal. In the case of remote archives, this action is permanent. You can't reconnect this user to the remote archive again.
[Y] Yes [A] Yes to All [N] No [L] No to All [?] Help (default is "Y"):
Y
Active Directory operation failed on LocalDCName.local.com. This error is not retriable. Additional information: The parameter is incorrect.
Active directory response: 00000057: LdapErr: DSID-0C090CB9, comment: Error in attribute conversion operation, data 0, v2580
+ CategoryInfo : NotSpecified: (:) [Disable-Mailbox], ADOperationException
+ FullyQualifiedErrorId : [Server=LA-MBX01Server,RequestId=6ed97c1e-ae68-4670-a097-c4e65f683274,TimeStamp=11/18/2014 7:50:07 PM] [FailureCategory=Cmdlet-ADOperationException] 8D6C0FEB,Microsoft.Exchange.Management.RecipientTasks.Disable
Mailbox
+ PSComputerName : LocalDCName.local.com
I captured everything with the START-TRANSCRIPT cmdlet and changed the specific values to our organization (i.e., "[email protected]" and "LocalDCName.Local.com"). I've tried this on other mailboxes and I receive the same error whether
I use EMC or EMS. I believe this might be AD schema related just not sure where.

Getting error when I try to remove eum secondary email address from the Mailbox from Exchange 2013 server

Getting error when I try to remove eum secondary email address from the Mailbox from Exchange 2013 server. The command works if you issue directly from the server exchange shell.
I open the remote power shell to the exchange server 2013.
Issue the following commands and getting the following error.
$mailbox = Get-Mailbox -Identity testuser$mailbox.EmailAddresses -= "eum:50004;phone-context=telExt5digits.lync5.com"Then getting the following error:Method invocation failed because [System.Collections.ArrayList] doesn't contain a method named 'op_Subtraction'.
At line:1 char:27
+ $mailbox.EmailAddresses -= <<<< "eum:50004;phone-context=telExt5digits.lync5.com"
+ CategoryInfo : InvalidOperation: (op_Subtraction:String) [], RuntimeException
+ FullyQualifiedErrorId : MethodNotFoundHelp!

Now for an answer - your remote session doesn't have the same object you have on the server itself. Notice it says this is an array list, not a ProxyAddressCollection. If you need to work around this, you'll need to massage the addresses another
way that the system will accept. I'd try the following:
$NewAddresses = $mailboxEmailAddresses | ? { $_ -notlike "eum:50004;phone-context=telExt5digits.lync5.com" }
See what you get in the $NewAddresses variable when you do this.

Outlook password prompt for mailboxes on Exchange 2013 CU1

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