Hi Cowboy59,
Thanks for posting here with such detailed information.
From your description, I understand the search function of Outlook for Mac 2011 doesn’t work, and you have tried the following troubleshooting steps and till now haven’t have the issue resolved:
1. Uninstall Office 2011 suite and re-install.
2. Force spotlight to re-index.
3. In spotlight preferences, disable mail, reboot, enable mail and reboot.
4. Rebuild database.
Because the search function in Office 365 OWA (Outlook Web App) works well, it proves that the “search” function service on the server side is OK. So let’s focus on troubleshooting the issue on the affected Mac. To identify the root cause of this issue, I would recommend you do the following attempts:
1. Set up the affected account on another PC/Mac to see whether the same issue occurs.
2. If another PC/Mac works well, please check whether the Mac Operating System and Outlook for Mac 2011 have had all the patches up to date. This is used to rule out the effect of not fully patched clients.
3. Sometimes the anti-virus software could lead to this kind of issue. Please disable anti-virus software on the affected Mac to see whether this issue still occurs.
4. Could you try another network environment?
5. Please try configuring a non-Office 365 account to the Outlook for Mac to see whether the same issue occur.
Regards,
Xinyu Zhou