How do I Send Backed up Emails from Mac on Outlook to my new Office 365 Account? I have tried everything and have had no luck!

Hello

I was wondering if someone can assist me with a reoccurring issue I have been having all week.This would be very much appreciated as I have been so stressed about this all week! :(

Everything below is based on performing on a MAC computer:

I have all of my old emails in Outlook backed up before I switched to the new Office 365. When I exported my emails and saved the .olm file onto my desktop, I was told to import that file back onto Outlook and then those old emails (the ones backed up onto Outlook originally) should show up on my Office 365 as well.

I have tried so many different solutions to fix this and make it work as nothing happens when the import happens. All emails end up being in the same place as before without any changes and then only new emails keep coming into both Outlook and Office 365 from the minute I made the switch.

How can I get my old emails that I backed up onto my Outlook to appear on my Office 365 as well? Outlook has both old backed up emails and new emails coming in but Office 365 only has the new ones.

What I have tried and still didn't work:

1. Creating a new identity and doing the import and export again through that identity

2. Overriding the original export with a new one that I redid and importing that again

3. Searching in "On my computer" to get the files but it constantly appears as being empty

Can you please help me!!?? :(

Thanks

Joanna