same problem here but finally found what works for me. I reindexed, I removed my account and added it again, I even migrated my laptop all over again and nothing. Finally what worked was instead of adding the "Main Profile" to the privacy list to reindex..I added the "Macintosh HD" to the privacy list, restarted my laptop, then went back to the privacy tab, removed "Macintosh HD" and then let my laptop sit for about an hour(make sure it doesn't turn off) and FINALLY FINALLY it works. I can search my emails on outlook. If you click on finder, on the list on the left under locations, right click on Macintosh HD "show enclosing folder" then you will see Macintosh HD with the disk image next to it. drag that to the privacy tab. Really hope this helps you all. I spent 2 long days trying to get this figured out. I am using MBPro 16" Monterey 12.0.1 16.55 version outlook. and I kept the old outlook, not the new one.

same problem here but finally found what works for me. I reindexed, I removed my account and added it again, I even migrated my laptop all over again and nothing. Finally what worked was instead of adding the "Main Profile" to the privacy list to reindex..I added the "Macintosh HD" to the privacy list, restarted my laptop, then went back to the privacy tab, removed "Macintosh HD" and then let my laptop sit for about an hour(make sure it doesn't turn off) and FINALLY FINALLY it works. I can search my emails on outlook. If you click on finder, on the list on the left under locations, right click on Macintosh HD "show enclosing folder" then you will see Macintosh HD with the disk image next to it. drag that to the privacy tab. Really hope this helps you all. I spent 2 long days trying to get this figured out. I am using MBPro 16" Monterey 12.0.1 16.55 version outlook. and I kept the old outlook, not the new one.