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Scenario / Question

Calendly isn’t integrating with my Outlook calendar. Events aren’t blocking off my availability or adding to my Outlook. How do I fix this?

 

Overview

Most Outlook issues come down to either an incorrect calendar connection or how busy/free status is set. Calendly only treats events marked Busy on your connected calendars as conflicts, and will book over events marked Free. If events aren’t adding to Outlook at all, disconnect and reconnect your Outlook/Office 365 calendar from Calendar Connections and choose the correct calendars to check for conflicts and to add new events to.

 

Step-by-Step

  1. Confirm your availability setup: Make sure your Availability Schedules in Calendly reflect when you want to be bookable. Calendly shows availability based on these schedules and your calendar conflicts.
  2. Verify your calendar connection: Go to your account menu > Calendar Connection (Calendar Connections page). Confirm you’re connected to the correct provider (Office 365/Outlook.com or Outlook via plugin/Exchange). If in doubt, disconnect and reconnect.
  3. Choose calendars to check for conflicts: On the Calendar Connection page, select Edit under Check for conflicts and select all Outlook calendars and sub-calendars that should block availability. Calendly only blocks times for events marked Busy on the calendars you select here.
  4. Ensure events are marked Busy in Outlook: Open example events in Outlook and confirm their Show As status is set to Busy. Free events will not block availability and can be booked over. Update any all-day or multi-day items to Busy if they should block time.
  5. Set where new bookings are added: In Calendar Connection, select the single calendar where Calendly should add newly scheduled events. Calendly can only publish to one connected calendar at a time.
  6. Re-test booking: Use your booking link to schedule a test. Confirm the time is removed from your booking page and that the event appears on the selected Outlook calendar and under Scheduled Events in Calendly.
  7. If using the Outlook desktop plug-in: Ensure the plug-in is installed, running on your Windows computer, and set to real-time sync. The plug-in must be running and your device online to sync. If it’s not needed, prefer connecting directly to Office 365/Outlook.com for more reliable, real-time syncing.

 

Key Notes & Limitations

  • Calendly only blocks times for events marked Busy on calendars selected under Check for conflicts. Free events do not block availability.
  • You can publish new Calendly events to only one connected calendar at a time. Choose the correct destination in Calendar Connection settings.
  • Outlook “Free” holds, FYIs, or tentative items that are not Busy will not block time. Update them to Busy if you need those times protected.
  • If your Outlook add-in/plugin or calendar connection is unstable, connecting via Office 365/Outlook.com is generally more seamless and reliable than the Windows desktop plug-in.

 

Related Questions (FAQ)

Q: Calendly shows me available even when I have Outlook events at that time. Why?

A: Check that those events are marked Busy and that the specific calendars containing those events are selected under Check for conflicts on the Calendar Connection page.

 

Q: Can Calendly read “Free” Outlook events and show them as open slots automatically?

A: No. Availability is controlled by your Calendly Availability Schedules. Calendly only reads Busy events to remove times within your set availability.

 

Q: My bookings aren’t appearing on my Outlook calendar. What should I do?

A: Disconnect and reconnect your Outlook/Office 365 calendar, then choose the single calendar where new bookings should be added. Re-test after reconnecting.

 

Links & Resources

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