Calendar items not showing in Outlook To-Do Bar

I'm using Outlook 365 desktop version, and I have my iCloud personal and shared calendars synced into Outlook. I can see, edit and change those items in Outlook Calendar. But nothing shows up in the To-Do Bar when I'm in the mail tab. If I go to View and select To-Do Bar, both Calendar and Tasks are selected, so I see them on the To-do Bar, but the iCloud events don't show up.

I've searched both this forum and the web and so far, I haven't found a solution.

Thanks