Issues with Calendly and Outlook Meeting Sync for Demos

·Aug 27, 2025 08:26 PM·

👋 Is anyone here using Calendly to book demos? We’re running into an issue where, if a user books through Outlook, the meeting doesn’t automatically appear on their calendar. This doesn’t happen with Gmail, it works fine there. As a result, we're seeing higher no-show rates with Outlook users to demos. Any thoughts on how to fix this?

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Hasnain R.
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That’s a common Calendly + Outlook quirk. A quick fix is making sure the Outlook add in is enabled, since without it events sometimes don’t auto sync. You can also set reminders in Clay/your CRM to reduce no shows. Some teams even add a “please add to calendar” step in the confirmation email as a backup.

Hasnain R.
·
·
That’s a common Calendly + Outlook quirk. A quick fix is making sure the Outlook add in is enabled, since without it events sometimes don’t auto sync. You can also set reminders in Clay/your CRM to reduce no shows. Some teams even add a “please add to calendar” step in the confirmation email as a backup.