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Hi Calendly Community,

I’m trying to set up automated email reminders for external clients (not in my Calendly org) using Workflows, but the emails aren’t sending consistently. I’m on the Standard plan with Google Calendar integration.

Details:

  • Setup: Calendly Standard plan, One-on-One event type, Google Calendar connected, notifications set to no-reply@calendly.com.
  • Issue: Workflow configured to send a reminder email to external clients 24 hours before meetings. Some clients receive it, others don’t (e.g., Gmail vs. Outlook).
  • Steps Tried:
    • Set up “Email Reminder to Someone Else” Workflow in Event Type settings (June 28, 2025).
    • Verified email addresses in booking form (no typos).
    • Checked Workflow settings: trigger is “Before event,” recipient is “Invitee email.”
    • Tested with my own Gmail and Outlook accounts; Gmail received, Outlook didn’t.
  • Environment: Latest Chrome browser, Google Calendar sync active, no spam flags in logs.

Is this a known issue with Outlook delivery or a Workflow config problem? Any tips to ensure reliable email delivery for external clients? Thanks for any help!

Hi ​@Bhola81736 - Thanks for reaching out!

The main error I’ve seen in the past is that the recipients email server rejects the workflow from being delivered, but there could be a few different things that could of happened.

I’d actually recommend reaching out to our support team on this, they’ll be able to investigate exactly what happened with each email. You can either chat in with them directly, or email support@calendly.com

 

Let me know if you have any questions!

Thanks for the reply and suggestion! The email reminder issue for external clients is fixed now. I adjusted the Workflow to use a custom “From” email (instead of no-reply@calendly.com), and now emails are delivering to both Gmail and Outlook consistently. I suspect Outlook was rejecting the default address, as you mentioned. I’ll reach out to support@calendly.com if it happens again. Appreciate the help! 

 

Best,
David James ( Founder of TheYesNoButton ) 

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