With the release of Outlook Hotmail Connector 14 for Office Outlook 2010, users of Microsoft Office Outlook Connector 12 for Office Outlook 2007 or Office Outlook 2003 may receive an upgrade offer when opening or starting Outlook in a Microsoft Office Outlook Connector upgrade window which has the following two options: Upgrade Now and Remind Me Later.

If user clicks on “Upgrade Now” option, the Outlook Connector auto-upgrade setup will connect to Microsoft server to download OLC.msi file. However, after finished downloading the Outlook Connector upgrade file, the setup installation window will briefly appear before disappearing and a window pops up with the following message to prompt for restart of Outlook 2003 or 2007:

Microsoft Office Outlook will now be restarted to complete installing the latest version of Outlook Connector.

The problem is that after clicking on OK button and restart Outlook, users of Outlook Connector will be prompted to upgrade again even after the upgrade setup process has been completed with Outlook restarted. The cycle repeats repetitively in endless loop. Or, the upgrade of Outlook Hotmail Connector simply fails.

Microsoft announced that the problem is caused by an issue with the Outlook Connector 12.1 auto-upgrade software, and has since temporarily turned off all auto-upgrade prompts.

Users can opt to continue using Outlook Connector 12.1, or you can upgrade manually to Outlook Hotmail Connector 14.0. In both cases, Outlook will successfully synchronize with Windows Live Hotmail Inbox.

For users who have already performed the auto-upgrade of Outlook Connector, try the following steps to fix and resolve the upgrade issue:

  1. Close all versions of Outlook, Hotmail and MSN (Windows Live) Messenger.
  2. Uninstall Outlook Connector from Add and Remove Programs or Programs and Features.
  3. Download standalone 32-bit version of Outlook Hotmail Connector 14 for Outlook 2003, 2007 and 2010.
  4. Install the new version Outlook Connector.
  5. Reopen Outlook.