Bookings only shows 2 appointments in month view if more than 3 scheduled.

This is a strange design flaw I believe. I am not sure if it can be overridden or if Microsoft needs to adjust.

If you look at "Month View" in bookings, but have more than 3 appointments scheduled that day, the month view will only show you 2 appointments UNLESS you click on that day. At that point it will show you the rest of the appointments in a new pane. The day in month view gives no indication that additional appointments exist though so users have no indication that there may be additional appointments they can't see without clicking into the day.

Also note, if you have exactly 3 or less scheduled on a day, than all the appointments for that day will show. Some of our calendar appointments have no staff assigned, which may be impacting things.

Week view and day view don't exhibit this behavior. 

Users expect experience similar to Outlook that shows a + sign in month view when more appointments exist than can fit in the box, so this will negatively impact users who are not aware).