TL;DR: In CalendarBridge, edit your sync connection and uncheck the All Private checkbox. If the calendar you are syncing to is set to only show “Busy” to others in your organization, then that’s all people will see from the synced events, even though they aren’t marked as private. The CalendarBridge documentation on how to configure the privacy settings of your event copies isn’t clear on this, in my opinion.
I have been using Copilot for Microsoft 365 for less than a week, so I’m still just scratching the surface of its capabilities. This morning, we had this little conversation:
Me: What’s my day like?
Copilot: I’m sorry, but I couldn’t find any information about your day. Could you please provide more details or specify a date so I can help you better? [Note: I was disappointed that it didn’t understand what I was asking. I think most other AIs would have been able to infer, especially since I asked this question in the Outlook Calendar side panel.]
Me: What’s on my calendar for today?
It told me about one appointment on my calendar for today. However, I was looking at it; I could see that there were two. I knew there were two.
Me: What other meetings do I have this week?
It correctly told me about everything else on my calendar for the week except for my other appointment for this afternoon.
Me: I thought I was getting my hair cut this week?
Copilot: I’m sorry, but I couldn’t find anything about a scheduled haircut in your calendar for this week. Is there anything else you would like to know?
Me: You don’t see the “Hair with Leisha” out-of-office appointment from 1:30pm to 4:30pm today?
Copilot: I’m sorry, but I couldn’t find any information about an out-of-office appointment named “Hair with Leisha” from 1:30pm to 4:30pm today in your calendar. Is there anything else you would like to know?

So, at this point I decided to open a ticket with CalendarBridge support and see if this was a known issue or just something that I was experiencing. They replied in about an hour and a half. (Thanks for the fast customer service, CalendarBridge!) They said:
Hi Ricky,
It is likely because you are syncing the events as “Private.” Edit your sync connection to uncheck that box and it will likely work.
Thank you,
The CalendarBridge Team
This was very disappointing news. I had read the CalendarBridge documentation on how to configure the privacy settings of your event copies, and I knew it said:
If this box is checked, then all event copies will be marked as private such that other users in your organization will see your event copies as simply “busy” in the Outlook Scheduling Assistant.
To me, this implies that the converse of this is true. That is:
If this box is NOT checked, then all event copies will not be marked as private such that other users your organization will not see your event copies as simply “busy” in the Outlook Scheduling Assistant.
Well, it turns out that this is only kinda, sorta, maybe true in specific circumstances.
It all depends on the Sharing and permissions settings of the calendar to which we are syncing.


If this is set at the typical Microsoft 365 default (i.e. People in my organization Can view when I’m busy), then “Busy” is all others will see on the events synched by CalendarBridge, even though they are not marked as Private.
If our calendar is shared with others where they are allowed to view titles and locations or view all details, that is where having our synced events marked as Private would prevent others from seeing titles, locations, and details.
Whichever is most restrictive (the privacy settings on the calendar, or the privacy settings on the event) is the one that will be honored. Setting it as Private in CalendarBridge ensures that no one else will see the information about the synced event, but that includes Copilot for Microsoft 365.
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