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Why Your Recurring Calendar Workflows Keep Failing and How to Fix Them

If you’ve ever screamed at your screen wondering why the heck your HighLevel workflows aren’t firing for recurring appointments—you’re not alone.

I’ve seen this one trip up everyone from solo consultants to 10-seat agency teams.

We recently hosted a 🔥 live troubleshooting call with Mario Aldayuz (our wizard of workflows over at HL Pro Tools), and this exact issue came up. 

It turned into a mini masterclass on how to fix HighLevel automation hiccups—specifically with recurring calendar events.

So, if your automations are acting flaky… Here’s what’s really going on—and how to fix it like a pro.

The Hidden Problem: Your Trigger Is Lying to You

Here’s what most folks do (and I used to do too):
They set their workflow trigger to “Customer Booked Appointment.” Seems logical, right?

WRONG.

That trigger only fires when a client books the appointment manually—as in, they go to your calendar and click the time slot themselves.

So what happens when:

  • You manually add a recurring event?
  • Is a booking duplicated or cloned?
  • A recurring event just rolls over to next week?

Yep—no workflow gets triggered. Nothing. Silence. 👻

The Fix: Use the Right Trigger

What you really want is the “Appointment Status” trigger.
It’s way more flexible and it actually listens for changes to appointments regardless of how they were created.

Key Idea: “Appointment Status” is your best friend for anything that repeats, gets edited, or needs logic applied across multiple instances.

It lets you set conditions like:

  • Appointment confirmed ✅
  • Appointment rescheduled 🔁
  • Appointment no-show ❌
  • Appointment completed 🎉

And that’s where the magic happens. 💥

Quick How-To Fix It

If you’re not sure where to start, try this:

  1. Go into your workflow settings
  2. Swap out “Customer Booked Appointment” for “Appointment Status Changed”
  3. Add a filter like “status = confirmed” (or whatever your flow needs)
  4. Test it with a recurring event!

You’ll instantly avoid 90% of the missed triggers you’ve been banging your head against.

Bonus Tip

If you’re dealing with complex recurring workflows (think: onboarding sequences, follow-ups, multi-touch outreach)… don’t just rely on triggers alone.

🧩 Add wait steps, conditional logic, and smart tagging** to keep things organized across multiple event types.

And if all else fails? Get in touch with the HL Pro Tools team—we literally build and test this stuff all day. 🙌

Want Automations That Actually Work?

I’ve spent way too many late nights trying to troubleshoot broken workflows—so you don’t have to.

Head over to hlprotools.com to grab proven snapshots, plug-and-play automations, and the exact tools we use to build scalable, smart systems inside HighLevel.

Do you want the HighLevel fast-track?

We bundled all the goodness we created for ourselves over the past 18 months into a complete training to sell more & retain clients longer with HighLevel®.

About HL Pro Tools

HL Pro Tools is the only white label HighLevel® support with a money back guarantee to help your agency sell more & retain clients longer.

Do you want the HighLevel fast-track?

We bundled all the goodness we created for ourselves over the past 18 months into a complete training to sell more & retain clients longer with HighLevel®.