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You can resolve this issue by rebuilding the Outlook index. To rebuild the Outlook index, you initially need to click on the search bar at the taskbar, next to the windows symbol and type Control and click on Control Panel to open. In Control panel window, click on Programs. Upon landing on the Programs segment, find and click on Programs & Features. Next, scroll down to navigate Outlook 2016 or your version of it. Click on Change from the top menu and select Quick repair, then repair. This is how you can fix Outlook Search indexing not working.
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outlook search not working