Shared calendar often stops syncing and only rebooting my Mac solves it

I use Outlook.com for email and calendar, and I have a Mac and iPhone where I use the built in Apple apps to manage my email and calendar. I often notice that changes I've made to the calendar on my Mac aren't showing up on my iPhone (or on outlook.com's website). The account is setup to use Push syncing, but when this happens, I'll try manually syncing (View | Refresh Calendars), quitting the Calendar app and restarting it, and just waiting a long time. However, once this starts happening, the only thing that works is rebooting my Mac. Once I do, the changes I made to the calendar show up immediately on my iPhone (and at outlook.com). Then it's fine for a few days until this happens again (about once a week).

It's a troublesome bug, because I can't trust that changes I make to my calendar are going to show up on other devices.

Is there any way to capture logging or any other diagnostic info to help troubleshoot this?

Thanks!