Hey there @CVFormatter.co80655 - thanks for your post!

To clear up some confusion, first, let’s go over the two types of invitee booking confirmations.

There are two types of invitee booking notifications: Email Confirmations & Calendar invitations.

1. With Email Confirmations, Calendly sends the invitee an email notification from notifications@calendly.com and has a reply-to address that's associated with your Calendly login email. You can modify this on Account Settings page.
2. With Calendar Invitations, your connected calendar sends the invitee a notification of the booked meeting which has a reply-to address that's associated with your Add to calendar email on your Calendar Connection page.

Note: Calendar invitations are not compatible with iCloud Calendar or the Outlook Plugin (for Windows users). Users with either of these calendar connections set up as their "add-to calendar" on their Calendar Connection page will be defaulted to Email Confirmations. 

You will not be able to both send a calendar invite and an email confirmation from notifications@calendly.com to your invitees from a single event type. You’ll choose either/or.

I suggest the following: 

• disconnect your Outlook.com/O365 calendar connection from Calendly
• clear your cache and cookies (steps below)
• reconnect your Outlook.com/O365 calendar connection to Calendly
• book a test event to see if it works as expected
• if it does, great! if not, see below

How to clear browser cache

If this does not resolve your issue, please reach out to our support team for more personalized troubleshooting. You can reach out to our support team, available 24/7 via live chat, by logging into your Calendly account > clicking “chat with us” in the bottom righthand corner.

I hope this helps!
 

Hi Kelsi,

My invitee couldn’t receive Email Confirmations from notifications@calendly.com. I tested it myself.

This happened after I switched my Calendly Login email to Microsoft Outlook (same email address, I only switched the Email/Calendar provider to Outlook). I’m using Macbook by the way.

I will try the steps you mentioned above.

Hey again @CVFormatter.co80655 -- thanks for the clarification! Usually, this issue is going to be on the end of the email provider/server, be that yours or the invitees’. If it’s all invitees it’s likely something going wrong with your connection. That said, that does not mean at all that it can’t be the Calendly integration. Please do try the steps I provided and if they don’t help, reach out to our support team so they can look into the deliverability issue more in depth for you! Good luck. Please let me know what happens -- I’ll be curious and rooting for you!