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The search function for Outlook is dependent on the native OS X Spotlight search function. Because the Outlook app on your computer synchronizes email from the server, a Spotlight re-index can help with search problems once the re-index is complete.
There are a couple of thing you can do:
- Run the Outlook for Mac Search Repair Tool.
- Force OS X to re-index the content of your Mac (i.e. Macintosh HD)
- While waiting for the Macintosh HD re-index to happen (it can take some time), searching for emails via bwa.dartmouth.edu is the way to go.