Hey there @Sissel Wetteland - great question, and thanks for posting this topic! 

Firstly, when you say “Outlook” which type of calendar connection are you referring to? If you are using our O365 and/or Outlook.com calendar connections, there’s an easy solution here called “sync cancellations” that I’ll go into detail about! If you are using our Outlook Plugin, this option is not available. This means that deleting/cancelling an event from your Outlook Desktop Calendar will not translate over to Calendly, and you will need to also go into Calendly to cancel that event for you and your invitee to notify them and free up the time slot. 

To detail the “sync cancellations” feature I mentioned above: 

Calendly's Google and Office 365/Outlook.com calendar connections offer a "Sync Cancellations" option. Users can access this by clicking "Edit" next to "Add to calendar" on their Calendar Connections page.

With this setting enabled, deleting or declining an event in the user's connected calendar cancels the event in Calendly. This setting is enabled by default. This is only specific to if the user deletes or declines the event via their connected calendar. If an invitee declines that calendar event, the meeting will not cancel within Calendly.

You would need to switch over to the O365/Outlook.com Calendar Connection if you are currently using the Outlook Plugin in order to use this feature. If you are already utilizing one of those calendar connections, you should be able to go in and make that change easily! I hope this helps!

You might also find the below community topic helpful! 

Hi Kelsi!

Thank you for your reply!

I use 

Outlook Plug-In (Windows)

Version: 170. Device Information: Windows 10. Last Synced: 13:41 - Wednesday, 24 January 2024

I should have been clearer in my question: The event was not added to Calendly at all, only to Outlook. Manually in my kalendar there. But the plugin seems to sync the availability in Calendly when I do that, which is a good thing when I want to be unavailable in Calendly but have private events in my Outlook. So there is a kind of syncing taking place when I ADD things to Outlook., but not when I REMOVE things from Outlook.

The time slot I had an event for was set to unavailable (or does at least not show up as available times in Calendly) when I created the event in Outlook. But when I delted the event from Outlook, the time slots are still not coming up as available times even though my Outlook calendar now is free.

I hope I explained my problem clearer now. :-)

@Sissel Wetteland ah, thanks for the clarification! That changes things completely. I thought that you meant that when you cancelled/deleted an event booked through Calendly from your Outlook Calendar it was not also cancelling/deleting in Calendly. I appreciate the additional information! 

You are right in that your Outlook calendar should sync availability over to Calendly, meaning, Calendly should pick up “busy” events on it and make you unavailable for Calendly bookings, and should allow bookings (within the availability that you set up in Calendly) when your Outlook calendar is otherwise free.

Firstly, you can use our Troubleshooting availability tool on your scheduling page in order to understand what's causing the conflict. I find it to be super helpful and it resolves most availability issues. Check out this tool to look at the dates/times in Calendly you aren’t showing as free when you should be to double-check what exactly is causing it. Perhaps there is another “busy” event on your calendar you’ve forgotten, perhaps there’s another conflict in Calendly (duration, buffers, availability and so on).

If that does not help you figure it out, read the following to take a deeper look at your calendar connection and how it works: 

Help Center article: Outlook Desktop Plug-in

Help Center article: Outlook Plug-in FAQ

You might also really benefit from switching to the O365/Outlook.com calendar connection(s) from the Outlook Plug-in (if possible). 

• Are you able to view your calendar when logging in here? If so, you should be able to successfully connect your Office 365 cloud-based calendar here!
  • Note: if you use an Exchange server, you’ll want to select the Exchange calendar connection option within Calendly instead. 
• Does your organization have specific security requirements that prevent you from utilizing a cloud-based calendar connection? If so, then the plug-in is likely your best/only option - and you can ignore the rest! 

I hope this helps! If you are still running into issues after troubleshooting and looking at these resources, I suggest logging into your Calendly account and clicking “help” to connect with our support team directly. They are available 24/7 and can provide more personalized support for complex troubleshooting! =) 

Hi Kelsi and thank you again for all your help!

I have tried the different options you have suggested. The Troubleshoot did in fact show that Calendly still “reads” the event from my Outlook calendar even though its been deleted days ago.

The solution is to change the calendar event to “free”. (As shown below) My problem is obviously that I have no event to change :-)

“CALENDAR

• What does it mean?
  • There is a "busy" event in your connected calendar at this time.
• How do you resolve it?
  • Change calendar event status from "busy" to “free” or cancel the calendar event”

 So what to do then?

I tried to connect to check if I could connect to the could-based calendar, but I could not. So I guess I have to stick with the plugin then.

My last resort is then to contact the support team directly. But when I click Help  and Contact us, the page seems to be not functioning. I cannot write anywhere…

Is there a link to how to contact the team directly and get personalized help, that you can provide?

Thank you so much again :-)

Hey again @Sissel Wetteland - so sorry this is still ongoing! I do have a question. Were the events you deleted created by you on your calendar originally, or were they shared by someone else (and created by someone else)? If the latter, they would have to be deleted or changed to “free” from the original host calendar in order to be reflected in Calendly. Additionally, do you have more than one calendar connection/more than one “check for conflicts” calendar? If so, check that out for “busy” events as well! The troubleshooting tool should tell you which calendar the busy event is on, however. 

I am sorry to hear you are having issues reaching out to our support team. There is no direct link - the most direct way to contact them is via your account. Based on what you said, it seems like it might be an issue with your browser.

Try: 

1. A different browser (we suggest Chrome)
2. Clearing cache and cookies in your current browser (steps below)
3. An incognito/private browser window
4. Running any app (browser) and/or device (computer) updates and then restarting your computer
5. Restarting your computer after all steps and trying again in a new browser window

How to clear browser cache

After you’ve done this, try reaching out to our support team again! I hope this helps!