Difficulty Syncing Calendly with External Calendar Apps

I am having the exact same problem. Please help!!!!

My outlook items do not populate on my availability. What I mean by this is: next Monday I have a couple of meetings in my Outlook calendar, but I still have full availability with Calendly. It says my microsoft 365 is already merged to Calendly, but there is nothing populating.

I also stumbled upon one place there seemed to be certain calendars from my organization, but mine was oddly absent.

Firstly - sorry to hear this! You need to make sure of a few things, here. 

1. Calendly reads “busy” calendar events as conflicts by default - if they are marked “free” they will appear as available time slots in Calendly
2. With Outlook/O365 specifically, you can also set Calendly to read “tentative” and “away/OOO” and “working elsewhere” as conflicts
3. To see why you're free when you should be unavailable: go to your Calendly home page > select "account" and then "calendar connections" > at "check for conflicts" select "edit" > select all calendars that should be checked for conflicts to select the aforementioned settings

When it comes to the what you mentioned in your second comment: 

Yeah, I checked again using the method described in this post, but my name is not available in the calendars. Several of my coworkers populate in the check boxes, as well as calendars for certain rooms. However my name is not there.

This sounds like a shared calendar issue. 

Many organizations utilize shared calendars within their connected calendar platforms. More information from each platform:

• Google: Share your calendar with someone

• Office 365: Share your calendar in Outlook on the web

• iCloud: Share a calendar on iCloud.com

Generally speaking, Calendly can access shared calendars for which the user has read/write access. These calendars would appear in the "Check for conflicts" and "Add to calendar" menus on the Calendar Connections page.

For context, Calendly will display the first 10 subcalendars that Microsoft sends us in the check for conflicts and add to calendar sections (please see below):

If you have more than 10 shared/sub-calendars, that may be why you are not seeing your preferred calendar(s).

Are you able to temporarily remove some of the calendars you currently have subscribed to see if that switches which calendars display in Calendly? You may need to disconnect + reconnect your calendar from your Calendar Connections page to update the display. Alternatively, some instances of O365/Outlook calendars will allow you to drag and drop your calendar list to rearrange it. Could you give this a try from your calendar, then refresh your connection within Calendly on the Calendar Connections page?

Once you are able to view the correct subcalendars, you can select up to four subcalendars to be checked for conflicts.

If your sub calendar is not appearing under “check for conflicts” I would recommend sharing this calendar from Outlook on the web (outlook.office.com/calendar), following these instructions from Microsoft: https://support.microsoft.com/en-us/office/share-your-calendar-in-outlook-on-the-web-7ecef8ae-139c-40d9-bae2-a23977ee58d5. This has a different result than sharing the calendar through the Outlook desktop application, which should in turn allow Calendly to access the calendar. You'll want to specifically ensure that you have Can edit permissions in order for Calendly to access this calendar. (You may need to ask the individual who shared this calendar with you to confirm this on their side if you cannot access this information on your side.)

As an additional point of reference, here is a third party article that walks through the process of sharing your calendars via Office 365 online: https://support.greenhouse.io/hc/en-us/articles/360007604032-Outlook365-Can-t-See-Shared-Calendars.

I hope this helps! If you are still having issues after looking into all of this, you might need more individualized support. In this case, please log into your Calendly account and click “help” to get in touch with our support team, available 24/7. 

Yayyy! I am so glad that helped! Back to easy scheduling you go!