[jammacade.com]

I was able to troubleshoot some more and found out a workaround for my issue:

When clicking the "x" in top right to close the Outlook, it was shutting Outlook down. I changed it so the "x" just closes (but it stays running) Outlook. Now when I receive an email it sends notification. This will probably drain my battery faster, but that's a trade off I can live with.