Does Outlook 2010 support expired password, or password reminder?
Some of our users upgraded to Outlook 2010 and they said if their accounts have "User must change password at next logon" enabled, they would not be able to logon to Outlook 2010, they would see the repeated the password prompts. They have to use OWA or Outlook 2007 to get the password expired dialog box.
Does the issue occur to some specific users or all users in your organization?
May I know your Exchange version?
Does the issue reproduce when they start their Outlook by safe mode?
Does the issue persist when they recreate their profiles?
And here is a KB article for you.
Save password setting not retained in Outlook or Outlook Express:
Hope it helps.
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The problem affect Outlook 2010 + Exchange 2003 and Exchange 2010 users as long as the Windows logon id is different than the mailbox. If Integrated NTLM password is used, the user will get the invalid password warning and password change dialog box.
I did not try safe mode but the problem is very consistent. Once the "User must change password" option is disabled, the user can logon without any problem.
Issue persists after profile is re-created.