Hi ​@Greg58622 - Thanks for reaching out.

At this time, Calendly only adds events to one Calendar at a time, outside of sharing that Calendar via outlook, the best way to do this would utilizing Zapier to trigger Outlook to create a Blocking event whenever a Calendly event is created in your main Calendar. You can see here for more information: Connecting Calendly with Outlook with Zapier || Integrating Zapier with Calendly

I did some digging and unfortunately it seems that Outlook doesn’t allow for meetings to automatically populate in other calendars at this time either. So Zapier might be the best way to move forward.

Let me know if you have any questions!

Maybe we can move this to a feature request thread. It’s a major challenge for fractional professionals that represent multiple companies and juggling calendars to keep from double booking internal meetings. When a meeting is booked, I basically have to go into each company calendar and manually block it off as “Busy” so internal employees don’t book over a meeting I have with another company. Solve that issue and I’ll become an investor.

I appreciate the feedback, I’ll get this linked over to our product team to review, this makes a lot of sense. Thanks for the input here!