Exchange 2013/2010 Co-existance Outlook Users Always Prompted for Password

Hello,
We are in the process of attempting to migrate to Exchange 2013, but during the migration time, we need to coexist with the two versions. Our outlook clients are a mix of Office 2007, 2010, and 2013. When a user is migrated from 2010 to 2013,
they start getting prompted for their password in Outlook every few minutes. They can click cancel and continue working, but they continue to get prompts for their password. If they click the update folder button in outlook, it updates fine, and
the password prompt goes away for awhile.
Most topics on this state that this is caused by a certificate issue. We have an internally deployed CA, with the Root certificate trusted by all clients. The exchange 2013 server has a certificate that was created by this CA.
I believe that this is caused by OAB (address book) still being hosted on the Exchange 2010 server (with a self signed cert), that is causing the connection to fail. Is there anyway to test this without breaking outlook connections for the users that
are on Exchange 2010? Or is there any other reason that this would occur?
Thanks for any assistance.

Sorry for taking so long to reply, other items came up that rank higher then this migration.
I ran the Test-OutlookWebServices CMD and got this result:
[PS] C:\Windows\system32> Test-OutlookWebServices
Source                              ServiceEndpoint
Scenario                       Result Latency
(MS)
EXCHANGE13.company.local           exchange10.company.local           Autodiscover: Outlook Provider Failure     229
EXCHANGE13.company.local
Exchange Web Services          Skipped       0
EXCHANGE13.company.local
Availability Service           Skipped       0
EXCHANGE13.company.local
Offline Address Book           Skipped       0
I
am currently thinking that this may be the error. Is there a way to
change the first failing result to the hostname of the
exchange13.company.local without breaking the current settings for the
exchange10.company.local autodiscover?

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Outlook 2007 Clients Prompt For Password When Opening

I am running Exchange 2007 Standard. New outlook 07 clients prompt for password each time it is opened. Older clients do not prompt for password. Is there any way for outlook 07 to not prompt for password? Users already logged into domain, should their credentials not be recognized automatically like with outlook 03?

This fixed it for me.
http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/383d130e-869f-4fce-9502-8b340904b0ba/#636c5a5e-c61f-414b-8e85-562c888b83cc
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After Migrating To Exchange 2013 All Outlook 2010 Users Constantly Prompted For Password (BUT OUTLOOK WORKS).

I have two servers. One is Exchange 2010 and the other is Exchange 2013.
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The odd thing is it shows connected and they are able to send and receive emails correctly.
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Thanks, Luke Pickard

This can appear if Outlook clients are trying to connect to OAB virtual directory, and don't succeed for some reason. Mailbox and mailflow will work, but password prompt will appear when Outlook tries to contact OAB. Try to investigate in that direction.
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Exchange 2013 & 2010 coexist problem. Authentication Credentials Prompt in Outlook

Hello Forum
We have two Exchange servers coexisting together. A new 2013 and a old 2010.
Everything was setup with the help of the Exchange Deployment Assistant.
I have had alot of trouble with Outlook 2013 Prompting for credentials on Exchange 2013 Mailboxes. None of the 2010 Mailboxes expericence this popup.
I solved most of the popup issues with this by changing the ExternalClientAuthenticationMethod to ntlm.(from negotiate)
http://blog.gothamtg.com/2013/10/15/users-constantly-prompted-for-credentials-after-being-migrated-to-exchange-2013/
and installing this update for Outlook:
http://support2.microsoft.com/kb/2899504/en-us
Now 2013 Mailboxes Work without any anoying popups. Except when they try to open another users mailbox that is located on the old 2010 server or a shared 2010 calander.
The connection to Exchange 2010 is working if I input the users password, but should it not work without this popup too?
This connections name acording to Outlook is called: Exchange-Mail RPC/HTTP (remote [NTLM])
We use the same domain for external and internal autodiscover connections.
Test Exchange Connectivity Analyzer shows everything ok.
If i run
get-outlookanywhere | fl *external*
(2013 server)
ExternalHostname                   : webmail.domain.com
ExternalClientAuthenticationMethod : Ntlm
ExternalClientsRequireSsl          : True
(2010 server)
ExternalHostname                   : webmail.domain.com
ExternalClientAuthenticationMethod : Basic
ExternalClientsRequireSsl          : True
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For us, the changes made in IIS are permanent, there quite possibly is a powershell way of doing it but I am still getting to grips with PS myself so I don't know.
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get it working now.
https://social.technet.microsoft.com/Forums/exchange/en-US/92178beb-3310-4363-8848-d022a6e2a77f/basic-vs-ntlm-authentication-outlook-anywhere
http://www.sysadminlab.net/exchange/outlook-anywhere-basic-vs-ntlm-authentication-explained

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Exchange 2013 / 2010 co-existence - Outlook won't connect to Exchange 2010 mailboxes

Greetings! I have a lab set up at home where I have been testing co-existence of Exchange 2013 and 2010 for a future corporate upgrade project.
I am running into some odd behavior. Any mailbox that has been migrated to Exchange 2013 works just fine, however, when I try to set up Outlook for a mailbox still on Exchange 2010 I receive errors. OWA works just fine for these Exchange
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Any suggestions? Thanks in advance!

Hi,
Don´t disable IPV6 on an Exchange Server, it is, in my opinion not necessary - also applies for AD.
You can use your original SSL Cert for your new Ex 2013 environment.
In dns you want two host A records: mail.domain.com and autodiscover.domain.com
On your 2013 set your internal and external virtual directories to mail.domain.com
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Also set the autodiscover URI to your Certificate name ie. mail.domain.com
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Thanks. I wanted to give some additional info before I run any commands. I currently have an A record for autodiscover and it is pointed to the Exchange 2013 DAG/cluster IP. I have a 3 entries for mail.domain, for DNS round robin; basically
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IMAP users continually prompted for password when switching folders

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to elaborate on this issue a bit more.
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mailq_path = /usr/bin/mailq
manpage_directory = /usr/share/man
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Always Prompted for Password

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Outlook Clients for Exchange 2013 Prompt for Password

I have a co-existence of versions 2007 and Exchange Server 2013 CU2 and currently have the following problem:
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Hi,
Agree with Andy,you can change the ExternalClientAuthenticationMethod to NTLM,
In addition, I recommend you refer to the following article:
Users Constantly Prompted for Credentials after Being Migrated to Exchange 2013
Thanks.
Note: Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality,
safety, or suitability of any software or information found there. Please make sure that you completely understand the risk before retrieving any suggestions from the above link.
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Password prompts - Exchange 2013 RTM vs. [Outlook 2007 & Outlook 2010] - Fully patched

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1. Windows XP SP3 (fully patched), Outlook 2007 SP3 + Nov 2012 Patch - When launching Outlook prompts for password only once.
2. Windows 7 (fully patched), Outlook 2010 (fully patched) - When launching Outlook doesn't prompt for password.
I'm aware of this:
http://support.microsoft.com/kb/956531
The goal - Eliminate issue with password prompts for Windows XP.
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Memento Mori

Hi,
Based on my experience, the credential issue is mostly likely caused by authentication method.
And I recommend the following troubleshooting:
1. Change LmCompatibilityLevel on the windows XP client to a value of 2 or 3:
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Windows XP Machines Always Prompt for Credentials (Exchange 2013, Outlook 2010)

I am running Exchange 2013 on Server 2012 Datacenter (VM). Windows 7 clients with Outlook 2010 work fine. Windows XP clients with Outlook 2010 prompt for credentials (user name and password) each time Outlook is started, and checking the "Remember
my password" box does not prevent this from happening the next time. The "Always prompt for logon credentials" checkbox on the "Security" tab of the "More Settings" section of the Exchange account is not checked. I have found a myriad of posts
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I am hopefuly that the fact that this only happens on Windows XP will be telling.

Proxy settings:
auth_param ntlm program /usr/bin/ntlm_auth --helper-protocol=squid-2.5-ntlmssp
auth_param ntlm children 50
auth_param ntlm keep_alive on
auth_param basic program /usr/lib/squid3/squid_ldap_auth -R \
-b "DC=domain,DC=local" \
-D "CN=Squid Proxy,OU=TI,OU=Domain,DC=domain,DC=local" \
-W passldap \
-f "sAMAccountName=%s" \
-h domain.local
auth_param basic children 20
auth_param basic realm Domain Internet Proxy
auth_param basic credentialsttl 8 hours
external_acl_type ADS children=50 ipv4 ttl=60 %LOGIN /usr/lib/squid3/squid_ldap_group -S -K -b "DC=domain,DC=local" -f "(&(objectclass=person)(sAMAccountName=%v)(memberof =CN=%a,OU=Domain,DC=domain,DC=local))" -D "CN=Squid Proxy,OU=TI,OU=Domain,DC=domain,DC=local" -s sub -W ldappass domain.local
tks.

Exchange 2013 / 2010 coexistence with different public domains

Currently in my organization
1x Exchange 2010 Standard w/SP3 - Client Access / Hub Transport
1x Exchange 2010 Standard w/SP3 - Unified Messaging Server (we also have Lync 2013 in the environment)
1x Exchange 2010 Standard w/SP3 - Mailbox
In my organization, we have approximately 600 mailboxes - 100 office staff, and 500 field employees using a mixture of Outlook 2007/2010/2013 and various mobile devices. Most of our field employees are in remote locations, several hundred
miles away. We have no IT staff in any of our field locations.
We also have two public domains that we use, though we are trying to phase out the old one to unify everything.
domain-old.com - Used when the company had a different name. All Exchange services are published with this one.
domain-new.com - Used after the company changed names. The goal is to publish all Exchange services with this one.
domain.local - Our internal Active Directory domain.
We use Microsoft Exchange Online Protection for all inbound/outbound email. We publish OWA, ActiveSync, etc. through our Sophos firewall. Also, we have two KEMP LoadMaster appliances that for high availability that we currently use for Lync 2013; they are
severely underutilized.
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My primary goal is to introduce high availability into our environment by introducing redundancy on multiple levels. I would like to accomplish this by utilizing Exchange 2013 since we will need to purchase additional licensing anyway. My idea of the
final topology is:
2x KEMP LoadMaster appliances providing reverse proxy and load balancing to the CAS servers
2x Physical servers running Hyper-V, separated physically but in the same AD site. Each one would run:
1x VM with Exchange 2013 Standard w/SP1 - Client Access
1x VM with Exchange 2013 Enterprise w/SP1 - Mailbox - Utilizing DAGs for high-availability
I'd like all the new Exchange services to be published under the domain-new.com domain - such as mail.domain-new.com, mail.domain-new.com/owa, smtp.domain-new.com, etc.
We have purchased two new physical servers that will be Hyper-V hosts running Server 2012R2. My timeframe to start this project is within the next two weeks, so I'll be running the new Exchange 2013 VMs under Server 2012, not R2 as it won't be supported
until Exchange 2013 SP3 is released.
Deployment Plan
Install Exchange 2013 on new VMs.
Create CAS Array object.
Configure Exchange 2013 to publish under the new namespace.
Perform mailbox moves to 2013 for a small group (1-5 users) at a time. Recreate Outlook profiles and mobile device profiles for that group. Test and move to the next group.
Once all users are moved to the new namespace, decommission the Exchange 2010 servers.
Unknowns
My primary unknown is about the namespaces. All of the guides I have read strictly deal with keeping the existing namespace and having the Exchange 2013 CAS proxy requests to Exchange 2010 for mailboxes still on 2010. This should never be an issue for us
since we'll be using the new domain for each mailbox we move.
My question boils down to, is this a supported way to migrate to Exchange 2013? And if so, are there some materials or information to help me perform it this way?

Hi,
From the description, you want to install Exchange 2013 in another domain and then migrate from Exchange 2010 to Exchange 2013.
About DAG, all servers in a DAG must be running the same operating system. If there is only one mailbox server, there is no need to deploy DAG.
About CAS array, we should know that the CAS Array no longer exists in Exchange 2013.
About the namespace, based on my knowledge, we can introduce a new namespace. Just as what you said "This should never be an issue for us since we'll be using the new domain for each mailbox we move".
Here are some articles about how to upgrade from Exchange 2010 to Exchange 2013 in the same organization.
Checklist: Upgrade from Exchange 2010
Install Exchange 2013 in an Existing Exchange 2010 Organization
Upgrade from Exchange 2010 to Exchange 2013
Hope this helps.
Best regards,
Belinda
Belinda Ma
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.

Exchange 2013/2010 - Co-Existence, URLs.

Hey Team,
I am sure this is well documented and i for some reason cant seem to get good solid answer. But here is my questions. what are the correct URL settings for (OWA, ActiveSync, EWS) etc for Exchange 2013/2010 in a coexistence scenario?
1) All servers in the same ad site
2) mail. autodiscover, pointed to the 2013 server
3) 2013 server is internet connected.
Am i supposed to clear all the 2010 URLs?, Just the external ones? Use a separate namespace?
Thanks,
Robert
Robert

This is well documented in the below post, I would recommend you check it:
http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx
In Exchange 2010/2013 coexistence scenario, CAS 2013 will proxy all connections to Exchange 2010.
How CAS2013 Picks a Target Legacy Exchange Server
It’s important to understand that when CAS2013 proxies to a legacy Exchange Client Access server, it constructs a URL based on the server FQDN, not a load balanced namespace or the InternalURL value.
When a CAS2013 starts up, it connects to Active Directory and enumerates a topology map to understand all the Client Access servers that exist within the environment. Every 50 seconds, CAS2013 will send a lightweight request to each
protocol end point to all the Client Access servers in the topology map; these requests have a user agent string of HttpProxy.ClientAccessServer2010Ping
Mohammad Saeed Abdelaziz | MCSE 2003 | MCTS: Lync, OCS, Exchange2007 | CCNP | UC Voice Specialist http://lyncrocks.wordpress.com/

Outlook 2010 prompting for password

Hi everybody. I ran into an issue yesterday morning where at one of our sites Outlook 2010 has started prompting for a username and password. If the user types in their username as "MYDOMAIN\myuser" and their password, it lets them in but the Exchange
status shows as "Disconnected". If the user sets their username to just "myuser" without the domain on the front it lets them in and works as expected until they close Outlook, at which point they have to enter their credentials again.
The strangest thing about this is that it's only affecting one of our sites and only Outlook 2010. Users running 2007 and 2003 do not have the problem and only users at this physical location have the problem. Does anybody know where I can look? I have tried
clearing stored credentials, created new Outlook profiles and reset passwords. None of these things seem to have had any effect.

After changing a ton of outlook settings, deleting the user's account profile on outlook, deleting their domain profile from the effected computer, trying to fix the registry, deleting stored credentials, etc.... almost everything else I found something
that FINALLY worked for me after over a year and about 12 different users being effected.
in the past I would just give up after much frustration and upgrade them to Office 2013 but that gets very expensive especially when I have 57 other users that could potentially run into the same issue.
Here is what I did.
- back up the user's data. log out and log into local admin
- delete the user from the local registry
- repair Office 2010 through control panel/programs, restart
- have user log back in with their credentials to make new local profile. recover their backed up documents. log out and log back in as local admin.
- install hotfix KB2597011
- restart computer
- install hotfix KB2583935
-restart computer
- log in, open outlook and setup user's account.
Some of these steps may be skipped as I didn't find the hot-fixes until after I repaired office, however I am just providing what I did in the process to end up with a working outlook again.
Some things unique to my situation that may or may not help.
- I noticed some of the computers have Office2010 32bit installed on 64 bit machines.
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- For me this always happens when the user's passwords expire and they have to log in to the portal to change it. Then outlook starts with the repeated prompt for passwords. It is always computer specific and nothing but what I provided above has worked
other than re installing windows 7 and then office or upgrading to office 2013.

Exchange 2013/2010 Co-existance Outlook Users Always Prompted for Password

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