Outlook 2010 Authentication prompt

I have OUTLOOK 2010 connecting to Exchange 2010 (fully patched/etc. with proper CAS array settings/etc.).
We are seeing Password Authentication prompts from Outlook clients as they transition between a LAN connection to a Wireless connection. I have always attributed this to the client moving from MAPI mode to "Outlook Anywhere" mode, which in "Outlook
Anywhere" mode we have BASIC authentication enabled, so a prompt is expected (offsite is the concept).
HOWEVER since the workstation is moving from a LAN connection to a WIRELESS internal connection and the CAS array is available, WHY would I be seeing this prompt? My expectation is the workstation would stay in MAPI connectivity mode as it transitions from
the LAN connection to the wireless connection and no prompt would be expected?? Is it a "timing" issue?
THANKS

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.
I wont plagiarise others work but these two links here give a good explanation between Basic and NTLM. personally, I have always used basic because I always seem to get problems with NTLM, though one time it did work as expected but I forgot what I did to
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

Similar Messages

Outlook 2010 keeps prompting for password

Hi,
We use Exchange 2008 and Outlook 2010. For some reason, Outlook 2010 keeps prompting for password. My use entered the password and checked "Remember Password" box, but next morning when he logged in, he still got the prompt.
I removed the Outlook credential for Outlook listed under Password Credential in Control Panel, but still no help.
Please advise!
Thanks in advance!
Grace

Hi Grace
1. Open Outlook 2010. Click File>Account Settings>Account Settings.
2. Click the E-mail tab, click the Exchange Online mailbox, click Change…
3. Click More Settings…. Click the Security tab, make sure the Always prompt for logon credentials box is unchecked.
Please mark it answer if it helps you solving your problem
Amit Kotha

Outlook 2010 authentication pop up box won't go away

After we applied the latest round of Windows Updates to our guinea pig workstations, we discovered that one of them caused something to break in Outlook 2010. We are set to use AD auto detect authentication on a local Exchange 2007 server. The pop
up window has varied, and nothing we have done has fixed it, not even uninstalling all the patches. (After the first workstation had the bug, I installed the patches one at a time and determined its KB2553248 that breaks it.)
Mail flows normally and we can send and receive without any problems. The pop up box can be sent to the back but cannot be minimized.
Mine says:
Windows Security
Microsoft Outlook
Connecting to (my AD email address)
The OK button is grayed out. Hitting the Cancel button breaks the connection to Exchange, and causes "Connected to Microsoft Exchange" to change over to "Need Password" on the bottom toolbar. Clicking "Need Password" logs me in within a few seconds
without any further prompting.... but within five minutes the pop up box is back.
On the other user's computer, the pop up box says:
Windows Security
Please Insert a Smart Card
and prompts for credentials if she hits OK. Like my pop up, the window can be ignored and mail flows normally. If she hits cancel, her connection to Exchange breaks until she hits "Need Password" at which point she's logged right back in again.
Interestingly, her Outlook was never configured to authenticate with a smart card. Like mine, it's set to Auto Detect connection type and to configure with the Windows AD login information.
We're holding off deployment of KB2553248 until we have a fix for this. Although it does not impede mail flow it's annoying as heck, and our clients that use Outlook (all 500ish of them...) are sure to click Cancel and break their connection to Exchange
without knowing to click the Need Password again.
How can we hide this pop up box?

OK...update on my issue (which is now RESOLVED!!!) since other people may did what I did.
I looked at the following link:
http://demazter.wordpress.com/2010/02/09/outlook-continually-prompting-for-username-and-password-2/
None of the above worked...even the kerberos method.
OL 2010 pop up box didn't say anything about connecting to where. So I looked closely at the popup box for OL 2007...keeps on saying connecting to mail.company.com. I was wondering why OL was trying to go outside instead of exch2010.domain.local
even though my account settings/profile is set to exch2010.domain.local.
As I was reading an article on SCP and how to locate it using adsiedit (which I couldn't figure out how),
http://blogs.msdn.com/b/douggowans/archive/2007/06/28/serviceconnectionpoints.aspx
This line in the blog got me thinking:
This url can be changed using the set-clientaccessserver cmdlet with the parameter -AutodiscoverServiceInternalURI.
That InternalURI got me thinking. When I looked at a txtfile that I jolted down and saved of what I did during the install of Exch 2010,
Set-ClientAccessServer -Identity "exch2010" –AutodiscoverServiceInternalURI
https://mail.company.com/autodiscover/autodiscover.xml
Set-WebServicesVirtualDirectory -Identity "exch2010\EWS (Default Web Site)" –InternalUrl
https://mail.company.com/EWS/Exchange.asmx
Set-OABVirtualDirectory -Identity “exch2010\OAB (Default Web Site)” -InternalURL
https://mail.company.com/OAB
I figured, let's try changing them to:
Set-ClientAccessServer -Identity "exch2010" –AutodiscoverServiceInternalURI
https://exch2010/autodiscover/autodiscover.xml
Set-WebServicesVirtualDirectory -Identity "exch2010\EWS (Default Web Site)" –InternalUrl
https://exch2010/EWS/Exchange.asmx
Set-OABVirtualDirectory -Identity “exch2010\OAB (Default Web Site)” -InternalURL
https://exch2010/OAB
I entered those commands in EMS and executed them...then I loaded up OL 2010 and OL 2007. It's been 30 min and nothing has popped up!!!
Silly me..I think why I did mail.company.com was that I was following a couple of guides that were posted out there on the internet on exchange 2010 and they just entered mail.company.com into there. But I think their guides are for networks where
the internal domain and external domain are the same. ie company.com for both insdie and outside.
I am going to install KB2553248 back onto my Win 7/OL 2010 workstation and see if that breaks it.

Outlook 2010 keeps prompting for password every morning

Hi,
We run Exchange 2007 on Windows server 2008. All SP and updates are up to date.
About a month ago, two users got prompt for user credential in Outlook every morning, but other users in the domain are fine. Below are what I have tried but no help.
1. Deleted user credential for Outlook in Credential Manager
2. Recreated Outlook profile
3. Disjoin and rejoin their computers to the domain
I can repeat the problem on another computer with the user's account log in.
The problem only happens in the morning, once the user entered the credential, Outlook starts to update new email and it will be fine for the rest of the day.
Only two users have this problem. I can't figure out if they have anything in common. Since I can repeat the problem on another computer, I assume this problem should be related to user account.
I need help!
Thanks in advance!
Grace

Hi,
As per the information and details provided by you, to solve the Outlook 2010 password problem, please follow these steps: -
Firstly, you try to
change the profile.
Open Control panel/Mail/Select the profile and click Properties.
Select the mailbox and click the
Change button.
When inside the profile you will see tabs at top for
connection and security.
Please make sure you have selected
Negotiate authentication, and have unchecked the box that states
Always prompt for login credentials.
Then check if you are using
HTTP to connect with exchange, if so uncheck this and apply the changes.
Close Outlook if open and reopen Outlook.
I hope this information will be helpful for you.
Thanks and regards
Shweta@G
Hi Goyal,
Thank you very much for your reply. The Outlook settings are the same as you described. We do use HTTP to connect to Exchange. I unchecked it and see what happens tomorrow. but just FYI. All Outlook has the same settings with HTTP connection checked. Only
two specific accounts have the credential issue.
Will update you tomorrow.
Thanks,
Grace

Outlook 2010 keeps prompting for credentials

Hello,
I have just about every user experiencing an issue with Outlook 2010 where Outlook keeps prompting for credentials. This has been happening ever since recent Microsoft Office updates that rolled out last week it seems. All my users still have connection
to the exchange server and can send/reply just fine. Issue occurs on both 32 bit and 64bit versions. This prompt will appear every few seconds and is becoming a nuisance for all my users.
I have attempted the following with no resolution:
- removed credentials from credentials manager
- ran Outlook in safe mode
- ran repairs on Office
- completely removed and re-added users Outlook profile (profiles are manually configured)
- made sure Office is up to date
- configured Outlook account on freshly imaged PC

Hi,
For this issue, you can first try some suggestions in this forum content:
Why does Outlook keep prompting for password
Especially try NTLM Authentication to check the result.
We have received some report about this issue since the February 10, 2015 update for Outlook 2010 (KB2956128). If you have installed this update, please note we have realized this issue and once there is any update, I'll let you know.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs.

Windows XP with Outlook 2007 authentication prompt

We have successfully migrated some of our users from Exchange 2010 to 2013 - the ones running Windows 7 and Office 2007 and Office 2013.
We have some users with Windows XP and Office 2007 though and when they start Outlook they get prompted to logon to the mailbox. These are all domain connected PCs in a single domain. If they put their details in Outlook opens as normal but the next time
they start Outlook 2007 they get prompted again.
From looking around I suspect it is something to do with our UCC certificates.
The primary name is ourdomain.com
The alternate names are mail.ourdomain.com, mail2.ourdomain.com, ex2010.ourdomain.com and ex2013.ourdomain.com
I have tried setting EXCH and EXPR principal to ourdomain.com and the prompts remain.
Have we set the primary name wrongly ? Should it be mail.ourdomain.com ?
Any help appreciated
Darren

Windows XP is out of support, Microsoft doesn't test new technologies with oos platforms.
If you look around the web XP with any Office version has problem connecting to Exch 2013
This post is provided AS IS with no warranties or guarantees, and confers no rights.
~~~
Questo post non fornisce garanzie e non conferisce diritti

Outlook 2010 - new prompting for password

After installing Office 2010 Beta and working fine for about a month and a half, Outlook started prompting for a password. The machine is on the domain so the Outlook did not prompt before. If you cancel the prompt, everything seems to work fine. This happens on both Windows 7 64-bit and Windows XP. It started happening to all known users on Office 2010. The problem started on January 8, 2010.

I have searched all over for a solution to this crazy problem and some of them highly technical and poorly explained and were for outlook 2003 and 2007. Finally I found this less than 2 minute fix that works. http://www.howtogeek.com/howto/windows-vista/fix-for-outlook-2007-constantly-asking-for-password-on-vista/
This is not my fix but glad to pass along something that actually works. Give Kudos to the "how-to-Geek" and post in other forums to help out all your frustrated friends.
1. Close outlook!
2. go to my computer and then paste this into the address bar. %userprofile%\AppData\Roaming\Microsoft\Protect
3. rename the very long file name S-1-5......etc by appending "-old" to the end of the existing file.
4. now re-open outlook and you may be request for your password. If so enter it and check the remember password box
5. now go back to %userprofile%\AppData\Roaming\Microsoft\Protect by searching in windows explorer or my computer and you should see the renamed long named file
and a brand new long named file.
This should work for you. If not, then do a shut down and reboot a time or two. Then try reopening outlook 2010 and your problem should be fixed. Save
this link: http://www.howtogeek.com/howto/windows-vista/fix-for-outlook-2007-constantly-asking-for-password-on-vista/
because this problem is likely to recur sporadically because of microsofts pushed updates that cause more problems than they solve. Turn off automatic updates so MS cannot keep screwing up your system and snooping.
This fix was explicit for Vista but worked fine for me on Windows 7 64 bit running outlook 2010. Post your results to see if it works for others please. I know everyone is tired of chasing their tails on this problem and even posted fixes have
been so vague that you need to be a software engineer to follow them. If you have other fixes for this I know everyone would appreciate people posting all the steps from the beginning to end and assume that we know nothing at all. Post all the
paths and explanations in simple terms please.
I hope this helps.
Rick Nelson

Outlook (2010) & credential prompts

In my place of work I often see users complain that Outlook has 'randomly' forgotten their credentials, resulting in a pop-up dialog box with their username entered and a 'password'. This password is not their actual password: some users easily identify this as the character length is very different; some... don't.
The fix is usually asking them to enter the full AD name + re-enter their password manually, which reconnects them to Exchange.
My question(s): where is Outlook pulling this 'password' from and what causes it?
Configuration settings are that the authentication is done over RPC - with https used if network is slow (high-latency). Outlook password prompt is unchecked.
I've probably not included very much detail; if not sorry. If you do see this, i'd appreciate how you've fixed it?
This topic first appeared in the Spiceworks Community

Hi,
Thanks for posting in Windows Server Forum.
As this thread has been quiet for a while, we assume that the issue has been resolved. At this time, we will mark it as ‘Answered’ as the previous steps should be helpful for many similar scenarios. If the issue still persists, please feel free to reply
this post directly so we will be notified to follow it up.
BTW, we’d love to hear your feedback about the solution. By sharing your experience you can help other community members facing similar problems.
Thanks for your Support & understanding.
Regards.
Dharmesh Solanki
TechNet Community Support
Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Support, contact [email protected]

Unable to open documents in Office (Word and Excel) - 3 authentication prompts followed by 'Could not open ...'

I am getting multiple authentication prompts when I try to open or create a new .docx or .xslx document from SharePoint 2010.
I tried this on different machines and on different browsers (IE and Firefox) and see the same behavior. I am the site collection administrator. I see the same behavior on other sites also. Other users are also seeing the same behavior.
If I download the document, I can open it without any issues.
The Web Application IIS authentication settings is NTLM and Client Integration is enabled.

Hi shankze,
According to your description, my understanding is that you could not open the documents because of the authentications.
Go to IIS, make sure that the Security TokenServiceApplication pool is started.
Please do as the followings, and compare the result:
Add your site to the Trusted Sites Internet Zone.
Go to Internet Options - Security - Highlight the Trusted Sites Check Mark - click on custom level - scroll to the bottom and in the user authentication section select "Automatic logon with current username and password."
Also, you can do via group policy in DC server.
More information, please refer to the link:
http://www.networkadminsecrets.com/2011/08/sharepoint-2010-authentication-prompts.html
I hope this helps.
Thanks,
Wendy
Wendy Li
TechNet Community Support

Exchange 2010 mailbox prompts for authentication to Exchange 2013 mailbox

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
for authentication to the Exchange 2010 mailbox. Regardless of whether I entered the correct credentials or simply cancelled the prompt, I still had full access to both mailboxes (including Public Folders on 2010). The authentication prompt was removed with
the following command:
Get-OutlookAnywhere -Server my2013exchserver | Set-OutlookAnywhere -InternalClientsRequireSsl $true
The second issue I now have is the reverse of the above: an Exchange 2010 user is prompted for authentication to an Exchange 2013 mailbox. How do I begin to troubleshoot this problem - should I run the same command (above) on 2010? I don't quite understand
how Outlook communicates with Exchange but I am thinking there is an incorrect setting on one of the Virtual Directories(?).
Many thanks.

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:
Please check your connection authentication. We can run the following command to set your Outlook Anywhere for Exchange 2013:
Set-OutlookAnywhere -Identity "E15-01\Rpc (Default Web Site)" -InternalClientAuthenticationMethod Ntlm -ExternalClientAuthenticationMethod Basic -ExternalClientsRequireSsl $True -InternalClientsRequireSsl $true
In Outlook side, please ensure the following settings in Account Settings:
In Security tab, make sure Always prompt for logon credentials is unchecked and Logon network security is set to Negotiate Authentication.
Regards,
Winnie Liang
TechNet Community Support

Password prompts - Exchange 2013 RTM vs. [Outlook 2007 & Outlook 2010] - Fully patched

Exchange 2013 RTM - Multi-Tenant
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods : {Basic, Ntlm, Negotiate}
Clients using Outlook Anywhere only, not Exchange domain members.
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.
Any chance resolving this? CU install? Anything else?
Thanks.
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:
a. Click Start, click Run, type regedit in the Open box, and then press ENTER.
b. Locate and then click the following registry subkey:
HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Lsa\
c. In the pane on the right side, double-click lmcompatibilitylevel.
d. In the Value data box, type a value of 2 or 3 that is appropriate for your environment, and then click OK.
e. Exit Registry Editor.
f. Restart your computer
2. Reset the windows credential store.
If you have any question, please feel free to let me know.
Thanks,
Angela Shi
TechNet Community Support

Outlook 2010 Under Windows XP Requests Authentication After Each Launch

We are working on installing a new Exchange 2013 environment.
Exchange 2013 SP1 Standard has been installed and then upgraded to CU7. It is a single box for the CAS and MB roles. It is running Windows Server 2012 R2.
The domain and forest are in 2003 native mode, all domain controllers are running 2003 SP2 to meet the minimums. Errors logs have been evaluated, DCDIAG runs on all DCs with no errors and repadmin is showing replication is error free.
We have a mixture of XP (service pack 3) and Windows 7 Clients. Both are running Microsoft Office Professional Plus 2010
Outlook Version 14.0.6023.1000 (32-bit). The Windows 7 clients open Outlook normally and are not prompted for credentials. Windows XP clients are prompted for credentials once, each time they launch Outlook. This is our problem we need to
fix.
Clients under both Windows 7 and XP have no problem setting up the initial profile. It finds the autodiscover quickly and configures the profile.
Because we have separate internal and external domain names (cofm.com and mab.com) we purchased a SAN certificate from GoDaddy. It contains the following:
exchange.cofm.com (this is the cn)
autodiscover.cofm.com
exchange.mab.com
autodiscover.mab.com
OWA works fine under either https://exchange.cofm.com or
https://exchange.mab.com. Our users with Apple iPhones, Android and Windows phones have no problem creating connections to activesync.
Under the outlook clients, it doesn't seem to matter if we have selected cached exchange mode or not. We have changed the "Logon Network Security" to use Negotiate Authentication or Password Authentication (NTLM) and it doesn't seem to matter.
Under the connection status it shows HTTP for Directory and Mail connections.
If we "Test E-mail Autoconfiguration" it connects using the credentials we provide and no errors seem to show up in the XML results.
None of the permissions on the default virtual directories differs from "https://technet.microsoft.com/en-us/library/gg247612(v=exchg.150).aspx"
Any thoughts?
Again...the authentication prompt only occurs with our Windows XP clients running the Outlook 2010...not the Windows 7 clients. Switching the clients to Windows 7 or later is not in the budget atm.

Tried to look at/modify the providers
[PS] C:\Windows\system32>get-outlookprovider
Creating a new session for implicit remoting of "Get-OutlookProvider" command...
Name                          Server
CertPrincipalName             TTL
EXCH
1
EXPR
1
WEB
1
[PS] C:\Windows\system32>Set-OutlookProvider EXPR -CertPrincipalName:"msstd:exchange.cofm.com"
[PS] C:\Windows\system32>Set-OutlookProvider -Identity EXCH -CertPrincipalName msstd:exchange.cofm.com
[PS] C:\Windows\system32>iisreset
Attempting stop...
Internet services successfully stopped
Attempting start...
Internet services successfully restarted
[PS] C:\Windows\system32>get-outlookprovider
Creating a new session for implicit remoting of "Get-OutlookProvider" command...
Name                          Server
CertPrincipalName             TTL
EXCH
msstd:exchange.cofm.com       1
EXPR
msstd:exchange.cofm.com       1
WEB                                                                                                       1
No difference.

Outlook Anywhere Prompts for Credentials only for Outlook 2010, not Outlook 2013

I'm having a heck of a time with this one. We have Exchange 2010 on premise, with our filtering through EOP. Clients that are using Outlook 2010 Professional Plus are continuously getting prompted for credentials when off network and relying
on Outlook Anywhere.
I've read many threads about configuring credential manager appropriately for the internal domain and our external domain. I can get them to authenticate just fine, and email flows, but they continue to be prompted everytime they connect again.
Here is the kicker: When I install Outlook 2013 on the same computer, outlook anywhere functions just fine, no problems, no authentication prompt.
Like I said I have read a plethera of articles and threads about this, I have gone through all settings on Exchange, our edge server, our firewall, our certificate. The MSSTD string matches our "Issued To" string. NTLM authentication
is configured on both the client and the server. Appropriate settings are configured on the firewalls.
Anyone know why Outlook 2010 would have this problem, but not Outlook 2013 on the same computer, same user, same mailbox database?
Thanks in advance!!!

I'd still Echo Ed's original question.
Do you have Outlook 2010 patched up? At this time you need to be on SP1, and SP2 by October the 14th.
Also I expect you to have a recent update ontop of that as well.
http://blogs.technet.com/b/rmilne/archive/2014/04/14/office-2010-sp2_1320_-do-you-need-to-upgrade_3f00_.aspx
Cheers,
Rhoderick
Microsoft Senior Exchange PFE
Blog:
http://blogs.technet.com/rmilne
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Exchange 2003 - Continous password prompts in Outlook 2010

Hi.
A customer is experiencing continous password prompts in Outlook 2010. Outlook is configured against the Exchange 2003 BE server (FQDN) and Outlook Anywhere is configured to sync.customer.com with a valid 3rd party certificate.
Outlook is configured with Negotitate as Logon network security, setting this to basic/NTLM does not help. Connect to Microsoft Exchange using HTTP is set and configured with sync.customer.com, and msstd:sync.customer.com. All points checked except "On
fast networks, connect using HTTP first, then connect using TCP/IP", authentication is set to Basic. Changing authentication from Basic to NTLM seem to make the problem vanish.
Outlook Anywhere is functioning correctly and only prompting once for password when connecting from an external network. ISA is not configured for NTLM/Kerberos.
Exchange 2003 is located in main site in a resource domain. The prompts occur more often in two remote sites than the main site.
When opening Outlook RPCDiag shows established connection to BE and Active Directory, sometimes with prompt and sometimes without. After about 5 minutes the prompt may reappear, entering password does not remove the prompt, clicking cancel puts Outlook in
the "Need password" state, clicking this usually successfully connect Outlook to Exchange. Other times this just cause the prompt to reappear.
I´ve tried adding the internal and/or external IP address of the ISA server as sync.customer.com in the host-file on a client and forcing RPC/HTTPS through the DisableRpcTcpFallback, still getting the password prompts.
We have also been through the KB975363, changing the MaxConcurrentAPI on all domain controllers.
Finally, we know Exchange 2003 is in a unsupported state so there is no need to comment this.

Hi,
Firstly, I'd like to explian, basic authentication requires the user to enter domain, user name, and password. Thus, it's an expected behavior that the credential prompts once when the authentication is set to basic and it disappears when it's NTLM authentication:
http://technet.microsoft.com/en-us/library/aa996225(v=exchg.65).aspx
For the issue that the credential keeps prompting, I'd like to confirm if Outlook 2003 works well. If yes, you can refer to the following article:
http://support.microsoft.com/kb/927612/en-us
If all outlook clients prompt credential, you can check the RPC over HTTP connectivity by ExRCA:
https://testconnectivity.microsoft.com/
http://support.microsoft.com/kb/820281/en-us
Thanks,
Angela Shi
TechNet Community Support

Outlook Authentication Prompts

Having a lot of problems with Outlook 2010/2013 authentication prompts. Client is migrating from EX 2010 and going to onsite EX 2013. Both Outlook 2010 & 2013 get the prompts. At this point in the migration, all internal DNS records point to the load
balancer which goes to the 2013 DAG environment. I have verified the Outlook Anywhere settings on 2013 about 100 times.
External Host Name and Internal Host Name are identical: mail.company.com
External/Internal ClientAuthenticationMethods NTLM
IISAuthenticationMethods {Basic, NTLM, Negotiate}
Require SSL is true for both External/Internal
I have tried many things already, but I am still getting prompted. However, when I modify the local Hosts file to point to Exchange 2010 directly (for those users who are still on 2010), I get no prompts at all.
I have also tried pointing the hosts file to the 2013 servers directly, bypassing the load balancer and the prompts still happen. So, it is not the load balancer.
Thoughts?
MCITP Exchange 2010 | MCITP Lync Server 2010 | MCTS Windows 2008

Hello,
What’s the server name on the credential window? Is it the CAS server or MBX server?
How about manually canceled credential windows, can you still use Outlook to send/receive emails properly?
If the authentication failed when connecting to the CAS server, please check the authentication settings on each VDirs.
If the authentication failed when connecting to the MBX server, please check if the public folder migrated properly.
Thanks,
Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact
[email protected]
Simon Wu
TechNet Community Support

Outlook 2010 Authentication prompt

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