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,
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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 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 - 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 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.

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

Outlook 2010 prompt for credential when connecting to Exchange 2013 mailbox

I have 4 server Exchange 2010 with DAG and one server Exchange 2013, i've migrated some mailbox to the new 2013 server.
I'm having a problem with some Outlook 2010 that sometimes (not always) requires credential to connect to mailbox in a server Exchange 2013, but only
when Cache mode is enabled.
The client ask for credential and dont connect to mailbox until I change in online mode.
In Online Mode, everything works fine.
I don't have Public Folders, so the check box Download Public Folder is not selected and the authentication mode is "Negotiate".
Thanks in advance.
Elisa

Hi,
As far as I know, by default, shared mail folders not public folders are downloaded in Cached mode in Outlook 2010 and Outlook 2013:
http://support.microsoft.com/kb/982697/en-us
Please check if there is shared folder in the problematic Outlook 2010 client and try to check if the issue still exists with the same account on other Outlook client.
Best regards,
Angela Shi
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 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 2010 when deleting meeting attendees, not prompting to send to added/deleted attendees

Hello,
We have been having this issue for quite some time and I have endlessly searched the internet for answers as well as this forum but it doesn't seem like anyone has been able to help.
We are using Outlook 2010 and I have two employees who need to modify very large meeting invites, quite frequently. When they add an attendee to a meeting invite and click Send, it prompts them with the dialog box to send to only added/deleted attendees
or send to all attendees. When they delete an attendee and click Send, it does not prompt them with this dialog box and just sends to all on the invite. They are not modifying anything else within the invite, only deleting an attendee and we would like
to send to that attendee only. This is a major issue because these invites consist of anywhere from 30 - 75 Client (customer) attendees and it not only looks bad on our part, they start to get confused and annoyed when this continually happens.
Can someone PLEASE PLEASE HELP ASAP??? It does not appear that there is a solution out there for this issue.
Thanks in advance,
Lori

This is an interesting problem. You can go in to the Tracking area under the scheduling assistant and un-check anyone who has been deleted from the invitation list. When you save the meeting, it will ask if you want to send an update. However, it still does
not give the option of sending only to added or deleted participants. I just tried it and it did not send me an update after I deleted people on the invited list.
I hope this helps.

Outlook Negotiate/NTLM authentication credential prompt

Hello everyone,
I have been digging quite a while now for a solution to this but apparently there is not a lot of systems out there utilizing this or having problems with it. Here it comes:
We have a pure (no migration or coex) Exchange 2013 CU7 environment in production with 3 x CAS/MBX Servers (3 sites connected via WAN VPN). Inside our network our outlook clients (2013 SP1+) authenticate via Kerberos (ASA/SPN) to the Exchange Servers and
connect via MAPI over HTTP. Everything working fine!
External is a different Story: We have a Application Request Routing (ARR) machine in our perimeter network that forwards external users to the Exchange Servers and for a reason that I didn't manage to find yet I can't get it to work so that domain joined clients
(notebooks) that are outside the company's LAN would use their cached credentials to try to authenticate outlook against the Exchange Servers. Outlook always prompts the user for her/his password on start up and then connects fine. No problems after that -
PF, OoO, OAB - everything is working. If the user restarts the outlook -> password prompt once again and fine after that. Saving the credentials works but is obviously not the way NTLM/Negotiate is supposed to work.
So here is my progress on this:
I verified my virtual directory settings. Here is how the Mapi virtual directory looks like:
IISAuthenticationMethods          : {Negotiate}
InternalUrl                    : https://mail.domain.com/mapi
InternalAuthenticationMethods : {Negotiate}
ExternalUrl                     : https://mail.domain.com/mapi
ExternalAuthenticationMethods   : {Negotiate}
I've set everything to Negotiate because we don't have legacy Exchange Servers nor legacy mail clients in our network. I tried setting it to NTLM only which made the problem shift. Test clients connect to exchange and are able to view/receive mails but got
the infinite credential prompt and weren't able to access PF, OoO and OAB. Setting it to NTLM and Negotiate produces the same result as Negoiate alone.
Browsing https://autodiscover.domain.com/Autodiscover/Autodiscover.xml with IE (autodiscover URL set in intranet settings) gave the expected error code 600 without prompting for credentials. Even Firefox (network.negotiate-auth.trusted-ris set to domain.com)
is utilizing cached windows credentials and is able to log on to autodiscover and OWA with windows authentication enabled.
When a client has a valid Kerberos ticket cached (cmd -> klist) Outlook uses that ticket successfully even from outside the network but as soon as the ticket is gone (sign out and sign back in) Outlook prompts for user credentials again.
"Show connection status" in Outlook and the HttpMapi log on the CAS both show that Negotiate has been used for the connection. But why the password prompt then?
I read up on IIS ARR and it seems that it just passes through the authentication information when set to "anonymous authentication" which it is.
Now how I understand the auth method Negoiate in Exchange 2013 is that Outlook and the Server try to handshake on the strongest auth mechanism available in the following order: Kerberos -> NTLM -> Password Promt (Basic/NTLM) but in my case this doesn't
apply.
Now I would apprechiate it very much if someone could educate me in how this is supposed to work and if there is a mistake in my configuration or my understanding of the authentication process correct it.
A great day to everyone!
Vasko

I don't have a ton experiencing using something like ARR, but we should do some testing. The first thing I would try is to route around the ARR in the DMZ and connect directly to Exchange from externally. This SHOULD let us know where the problem
lies. If it succeeds (no auth prompts) then the issue is on the ARR and not Exchange. If it fails, then the issue is with the ARR and that needs to be looked at a little more clearly.
Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread

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
with similar issues, but they all seem to have to do with SBS/Exchange 2007, and I haven't come across something that works as a solution for me. One suggested certificate issues, and I was having certificate security warnings, but I got that resolved.
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.

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

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.
- Some of the users were swapped over using a profile mover program when we moved to a domain environment.
- 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.

Outlook (2010) & credential prompts

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