Outlook 2007: Outlook prompting for password issue

Symptoms: Outlook 2007 clients are prompting for password when connecting to Exchange 2007.

Possible solutions if affecting single users:

• Open the profile settings and make sure there is no checkbox in "Always prompt for user name and password" on the Security tab
• Check credential manager. It may be storing an incorrect password for the user and Outlook may be using this to connect to Exchange. Run control userpasswords2. On the Advanced tab, select "Manage Passwords". Remove any entries to the Exchange server. Alternatively, erase the server name and enter "S1" or the simple name of your global catalog server and leave the password blank. If prompted again, enter your username and password and check off "remember my password" one last time and it should not prompt again.
• Try typing in the username by including the domain name. i.e. DOMAINNAME\Username. This has been known to resolve the issue.
• In the task tray, hold down CTRL Key and right click the Outlook icon and select Test Email Auto Configuration. Uncheck Use Guessmart and Secure Guessmart Authentication. Click Test. When the test is completed, view the XML results.
• Check that the autodiscover URLs are in the proxy exceptions list.
• Open the following path: In Vista: \Users\YourUserName\AppData\Roaming\Microsoft Once open you will see numerous folders including a “protect” folder. Delete the “protect” folder. When you have deleted the protect folder, restart Outlook. You will be requested to enter your password again, but it will be the last time.
  Check that an Internet security product is not blocking a port.

Possible solutions if affecting a large number of people:

• Open IIS on theExchange server and checked the following directories under the default website: the root site, oab, autodiscover. Under the directory security tab, click Edit in the Secure Communications section. If you have "require SSL" checked and the 128 bit encryption, but under Client Certificates, it is set to ignore, then this may be the problem. Change this to "Accept" for each of the folders and restart IIS. This may not be a satisfactory solution for everyone.
• Try to connect to the autodiscover URLs listed in the SCP and in Exchange Management Console.
• Make sure the OABurl is set to https and not http
• In the task tray, hold down CTRL Key and right click the Outlook icon and select Test Email Auto Configuration. Uncheck Use Guessmart and Secure Guessmart Authentication. Click Test. When the test is completed, view the XML results. If the URL for the OAB is starting with HTTP instead of HTTPS then you may need to change this from the Exchange Management Console. Do an iisreset and test again.
  Make sure integrated security is enabled on the virtual directories where required.
• Ensure Offline Address Book has been migrated to Exchange 2007.
• Look at the properties of the autodiscover virtual directory and ensure a version of ASP is selected. If none is selected, clients may be prompted for password.
• Ensure Windows authentication is enabled on the Autodiscover virtual directory.
• See http://support.microsoft.com/kb/236032

If the problem exists when using RPC over HTTP:

If you are working RPC over https you are using or basic, or NTLM authentication, you need to be sure you are working NTLM. Now in order to ensure that outlook not uses any cached password we need to do the following. Go to Control Panel>User AcountsPress on Advanced Tab button. Click on Manage Passwords button. Review stored passwords , and if you see IP address of your mail server you should delete it.
Now we need to patch te registry
Click StartRun
Type regedit and press enter
Go to HKLM\SYSTEM\CurrentControlSet\Control\Lsa\
Find lmcompatibilitylevel DWORD parameter
Double-click on it and change its value to 3

Outlook: Offline Folder (OST) issues

This article lists many of the ways in which you can troubleshoot an issue with the Outlook offline mail file. This file is often refered to as an OST.

Determine more about the issue:

• Record the error messages that are appearing.
• An error at the beginning that asks if you would like to start in online or offline mode indicates that Outlook believes there is a discrepancy between the information in the OST and the mailbox.
• Record the steps taken in order to receive the error condition. In some cases, the computer has to be shutdown, disconnected from the network and restarted before the OST issue will reveal itself.
• Have the user log onto another computer and perform the tests using the same version of Windows and Office if possible.
• Create a new test user with mailbox on the computer where the fault occurs, and see if the same issues occur.

Try the following steps to resolve an OST issue:

• Ensure the user has read/write access to the OST file location.
• Create a new profile and at the same time, change the location of the OST. If there is autoconfiguration involved, there may be a %username% in the location. Remove this and replace with a real path instead, as well as setting a name for the OST that does not already exist in that location. When it asks to create a new OST, click Yes. Finish the profile creation and set it to open when Outlook is next opened. The error message should generally be resolved by this step.
• Shutdown Outlook and rename the OST file. Restart Outlook and check if the issue reoccurs. Note: If the user has been writing to their OST and it has not been synchronised to the server, you will lose this information. Try to determine first if this is the case.
• Create a new Outlook profile.
• If the user is running Outlook 2003, you may try upgrading to Office 2007. This has been proven to resolve some OST issues (where the OST itself does not appear to be at fault).
• Try performing an uninstall and reinstall of Office. This has been proven to not resolve some OST issues.
• Empty out the deleted items folder. Deleted items may have become corrupted or too large.
• Remove any delegates on the mailbox. Delegates may have become corrupted and/or orphaned.
• Export any inbox rules and then delete what is there. Rules can become corrupted. These can be re-imported when testing is complete.
• Right click on a folder in Outlook and select properties. Select the synchronisation tab and check if the folder has synchronised successfully. If the synchronisation tab is not available then you may not be in cached mode. See KB842284. To synchronise all folders, press Send/Receive All. To synchronise just a single folder, select the folder and select Send/Receive this folder only.
• Replace the Exchange server service support files for Outlook. In Office 2007, rename the C:\Program Files\Microsoft Office\Office12\emsmdb32.dll. Go to Add/Remove Programs, select Reinstall or repair, then Reinstall. In Offce 2003 you should rename emsabp32.dll, emsmdb32.dll, emsui32.dll, then reinstall Office. See KB842284.
• Try running the OSTScan tool to check for corruption. Run without the automatic repair first. It will create a report in the deleted items folder. Check the report for issues. Rerun the tool in repair mode if required. See http://office.microsoft.com/en-us/outlook-help/scan-and-repair-corrupted-outlook-data-files-HA010075831.aspx?pid=CH100788841033#BM2
• Try moving the mailbox to a new Exchange server if this is an option.