Hi @KeriBurns,

My knowledge of the internal working of Outlook calendars is limited but I can tell you that Calendly cannot override the internal settings of connected calendars. Calendly is really just a tool that sits on top of connected calendars and doesn’t control any of the internal rules for that calendar. It just schedules meetings based on someone’s availaiblity. If there are specific settings set up within Outlook to prevent bookings, Calendly doesn’t have a way of forcing a booking. That said you can tell Calendly to ignore certain meetings based on the name of that meeting. This would result in a double booking. More on that in Book over meetings.