Outlook 2010 & 2013 Password Prompts Randomly

Hi,
We have been upgrading workstations on the domain and new systems using Outlook 2010 and 2013 are getting prompted for their credentials randomly. Usually Outlook starts fine and connects, then at random times the user will be prompted and after entering
credentials it asks again and again. Sometimes this is fixed by simply closing and reopening Outlook.
The issue effects all upgraded users (Win 7Pro with Outlook 2010 or 2013).
I have tried some fixes, but I am open to any ideas or retrying any fixes in case they were not applied correctly.
Thanks,
Roger

Hi Roger:
Any help here:
Outlook Prompts for Password
If that is not it please reply with the version of SBS
Larry Struckmeyer[SBS-MVP] If your question is answered, please mark the response as the answer so that others can benefit.

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Hi,
Please check the problematic users' Outlook settings by the following steps:
1. Click File > Account Settings > Account Settings > Change > More settings.
2. In Security tab, make sure "Encrypt data between Microsoft Outlook and Microsoft Exchange" option is checked, "Always prompt for logon credentials" is unchecked.
3. Change the logon network security to Negotiate Authentication, and Apply > OK to set it.
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Thank you for the response.
I did as you suggested and the problem persists

Outlook 2010/2013 clients, outside of our main office, can't connect to our Exchange 2010 server

Hi,
Our remote users had been connecting to our Exchange server at our office since the Exchange server was installed in 2011.
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http://blogs.technet.com/b/rmilne/archive/2015/03/17/update-015_2d00_027-revised-_2800_3002657_2900_.aspx
For additional people reading this thread, please update to v2 of that update.
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Microsoft Outlook 2010 & 2013 cannot set automatic reply settings

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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.
Three of our users had mailboxes on Exchange 2013 for the last few weeks with no problems. They used Outlook 2013 and Outlook 2010. After moving the rest of our ~25 users to Exchange 2013 the users with Outlook 2010 began to be prompted for their
password constantly.
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I've tested our exchange connectivity using www.testexchangeconnectivity.com and all is well there.
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Luke
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.
Also, perform Outlook Configuration test (right click Outlook icon in task bar while holding CTRL and select Test email autoconfiguration.
Please mark as helpful if you find my contribution useful or as an answer if it does answer your question. That will encourage me - and others - to take time out to help you. Thank you! Damir

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Check your credential manager for any old passwords. Is this an exchange or pop account? Try changing your authentication method in outlook to use basic instead of NTLM and see if the popups disappear.
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Outlook 2010, 2013 on new 2010 exchange server get windows security popup for password

We recently migrated exchange 2003 on 2003 server to Server 2008R2 and Exchange 2010 SP3. The installation had multiple problems and we resorted to Microsoft technical support for the server resolution. On the server level it seems to function
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Please check the problematic users' Outlook settings by the following steps:
1. Click File > Account Settings > Account Settings > Change > More settings.
2. In Security tab, make sure "Encrypt data between Microsoft Outlook and Microsoft Exchange" option is checked, "Always prompt for logon credentials" is unchecked.
3. Change the logon network security to Negotiate Authentication, and Apply > OK to set it.
Restart Outlook to have a try. If the issue persists, please
re-create Outlook profile to check whether the issue persists.
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Winnie Liang
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Thank you for the response.
I did as you suggested and the problem persists

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Hi,
It is a known issue if you install the following security updates on March 10, 2015:
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Winnie Liang
TechNet Community Support

Why does Outlook 2010/2013 tries to connect by rpc over http in LAN?

Hi All,
I have Exchange 2010 (Two CAS) Published by TMG (Basic Authentication). Also outlook anywhere is configured with Basic Authentication.
Some users have issues with "authentication prompt" (randomly). By the way, Outlook Clients(2007/2010/2013) are fully updated.
What I can see when "authentication prompt" shows up, Outlook tries to connect by rpc over https.
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Jo

Hi,
Firstly, I'd like to say, basic authentication requires user name and password. Thus, it's an expected behavior that credential will prompt once when users login Outlook with basic authentication.
Additionally, I'd like to confirm how you confirm it's Outlook Anywhere when the credential prompts. Based on my knowledge, the credential issue may be caused by connectivity issue and we can confirm the connection method through the tool "connection status".
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ActiveX bypass in Outlook 2010 & 2013 for specially crafted html file

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Hi,
In case 3, what does it mean by "using Outlook.com as the email client"? Did you configure an Outlook.com account in Outlook client, or use Outlook.com account on web?
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We have a user who has these devices connected to our MX server;
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iPad
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Laptop Win7 Pro, Outlook 2013
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mode due to it being slower and having to wait if he loses the network briefly. Any ideas?

"So we disconnected all devices and reconnected all devices except his desktop. He ran the weekend with
no duplicates, Monday when we reconnected the desktop it came back strong."
"It seems to be tied to the cached mode and Offline use. I did a complete uninstall/re-install and turned off cached mode for the re-up
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Corey Carmickle

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Hi,
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Hi,
Did you take the pictures from Outlook 2010 or Outlook 2013?
I can find the picture below from Outlook 2013:
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Come back and mark the replies as answers if they help and unmark them if they provide no help.
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here

Outlook 2010 & 2013 Password Prompts Randomly

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