If you’ve ever connected a workstation to Office 365 and then been constantly prompted for your credentials you know how frustrating it can be.  Have you ever checked that box in Outlook to “Remember Password” and then screamed in frustration as yet another logon prompt came up?

Below is a collection of sites that can help you troubleshoot issues logging into your Office 365 account.

• ADFS / SSO issues:
  • Troubleshoot federated users being prompted at http://support.microsoft.com/kb/2461628
• Autodiscover issues:
  • Troubleshoot: Looping Credential Prompts When Signing In to Office 365 Using ADFS at http://www.youtube.com/watch?v=cfEQFK1SgU8
  • Coming from Exchange environments: make sure your Autodiscover DNS records (internal and external both) point to the correct place.  See also the Troubleshooting Autodiscover video.
  • Coming from BPOS (and possibly other Exchange systems) follow the instructions at http://support.microsoft.com/kb/2644437 to remove registry entries on clients that stubbornly don’t update their Autodiscover.
• Missing Updates:
  • Manually push out the updates using the instructions at http://community.office365.com/en-us/w/administration/manually-install-office-365-desktop-updates.aspx.  SCCM, WSUS and other configuration management systems will work just fine also.  There are download links of the bits for each package.  Make sure you get at least these three:
    • Microsoft Online Services Sign-In Assistant (IDCRL7)
    • Microsoft Office 2010 Update (KB2435954) – ALSO change the registry key noted in the link
    • Microsoft Outlook 2010 Update (KB2597011)
• Outlook Issues:
  • Uncheck “Always prompt for logon credentials” in Outlook (see http://community.office365.com/en-us/f/172/t/15620.aspx for details)
  • Recreate your Outlook profile – good steps at http://community.office365.com/en-us/f/170/t/22353.aspx
  • If Outlook discovers the wrong (old) Exchange system you have problems.  Use “outlook /rpcdiag” to ensure Outlook is connecting to Office 365.  You can also control-right-click on your Outlook icon in your system tray and choose the option for “Connection Status.”  You should see connections to the cloud-based e-mail servers, not legacy servers.  Good steps at http://www.petri.co.il/testing_rpc_over_http_connection.htm.
  • Outlook prompts for credentials when Exchange 2003 mailboxes access Free/Busy information for Office 365 mailboxes – http://community.office365.com/en-us/forums/162/t/3567.aspx
  • C:\Users\\AppData\Local\Microsoft\Sign In\Config\\Autodiscovery.xml.old not updating – rename or delete it as per http://www.brucebnews.com/2012/01/persistent-outlook-password-prompts-from-office-365/
• Windows, Networking & General:
  • Good Basic Troubleshooting: follow the instructions for Rich Authentication at http://support.microsoft.com/kb/2637629
  • Run (or reboot and rerun) the desktop setup wizard – steps at http://onlinehelp.microsoft.com/en-us/office365-smallbusinesses/ff637537.aspx
  • Change Internet Explorer security settings for Trusted sites & Windows Firewall to allow the sites listed at http://support.microsoft.com/kb/2637629
• Windows Stored Credential Conflicts & Issues:
  • Clearing out the Windows stored passwords for the user account under Control Panel – Users – Advanced or in the Credential Manager (depending on Windows version) – good troubleshooting at http://community.office365.com/en-us/f/172/p/52489/188561.aspx
    • XP see http://support.microsoft.com/kb/306541
    • Windows 7 see  http://windows.microsoft.com/en-US/windows7/remove-stored-passwords-certificates-and-other-credential