Hi everyone,
I’m working on a Calendly integration using the API and webhooks, and I want to make sure I fully understand how the webhook system behaves in real-world usage.
From the documentation, I understand that Calendly webhooks can be used to trigger events such as:
- Invitee Created (when a meeting is scheduled)
- Invitee Canceled (when a meeting is canceled)
- Routing form submissions
However, I’m a bit unclear about a few implementation details in practice:
- Do webhooks trigger instantly in all cases. or can there be any delay depending on the event type or plan?
- Are webhook events guaranteed to fire even if no one is actively logged into the Calendly dashboard?
- If multiple webhook subscriptions exist for the same event type, how is delivery handled?
- What is the best way to prevent duplicate processing when the same webhook payload is received more than once?
- Are there any recommended patterns for handling retries or failed webhook deliveries on the client side?
I’m building an automation flow where Calendly events need to trigger actions in an external system (via HTTP endpoints), so I want to make sure I’m handling edge cases correctly and following best practices.
If anyone has experience with production-level Calendly API + webhook setups, I’d really appreciate your insights or examples.
Thanks in advance!


