Hello, I just experienced something similar. After the Tahoe version 26.3.1 update (auto-initiated on my Mac) I lost a TON of information on my computer, not just in Outlook. I restored much of the info/files, but Outlook created a new instance and I had to add my 3 email accounts back, which restored all my current emails. But the emails stored in the "On My Computer" files were gone.
I spent 2 hours today with Apple trying to find the correct file to get those back, with no success. Called Apple back again and was told this is not an Apple issue, that I needed to contact Microsoft. Could not get through to a person at Microsoft so am turning here for some assistance.
I use Time Machine but I am not sure where exactly JUST my "On My Computer" files are stored, and once I find the correct file on my Time Machine backup, where do I put it on my outlook files to restore JUST those files and add to my already reconstructed new Outlook view? Can you advise here? Thanks.