Un able to transfer Outlook Calendar events to taskbar Calendar

As described in the title, I am unable to transfer ongoing event from my Outlook calendar to my taskbar calendar. To my understanding, there should be no reason why the two should be different, but I digress.

I initially thought that a quick reset of the taskbar calendar and then syncing it back would resolve the issue, but after doing so, I'm left with a bare taskbar calendar, and all my events remain on my Outlook calendar. If there is any way to make the taskbar calendar mimic the Outlook calendar, I'd appreciate some guidance