The Calendar Trigger Failure That Broke Morning Routines on macOS — And the Time-Based Trigger Patch That Solved It
It was a quiet Monday. Mugs of coffee were brewing. Alarms buzzed, laptops flipped open, and people everywhere were ready to conquer their day… until something weird happened on macOS.
Your “Morning Routine” shortcut didn’t run.
Your to-do list didn’t pop up. The weather didn’t show. The lights didn’t turn on. Your carefully crafted automation broke. All thanks to a sneaky little glitch in Calendar triggers.
TL;DR
macOS users were stunned when Calendar-based automations stopped working. Many routines, created using Shortcuts, depended on calendar events to trigger actions like turning on lights or reading out reminders. The root cause was a bug that broke Calendar trigger reliability. Thankfully, a clever workaround using time-based triggers got everything humming again.
What Is a Calendar Trigger Anyway?
Great question! A Calendar trigger is an automation starter.
It’s like telling your Mac or iPhone: “Hey, when this meeting starts, also do these other things.”
For example, you might have set up something like:
- Trigger: 7:00 AM Calendar Event — “Morning Routine”
- Actions:
- Read today’s weather
- Show today’s calendar
- Play your morning playlist
It made Mondays much better. And then… it all broke.
The Moment Things Went Sideways
For months, Apple’s Calendar triggers worked fine. But after a macOS update — possibly Ventura or Sonoma — people noticed something strange. Their automations weren’t firing. At all.
Even when the event time came and went, nothing happened.
Users on Reddit, Apple forums, and tech blogs began reporting the issue:
“My 7AM calendar-based Shortcut hasn’t run in three days. Anyone else?”
“Did Apple change something with calendar triggers?”
Yes, they did.
So, What Went Wrong?
Calendars rely on precise syncing and background processes. Miss one part of the chain — like a calendar not syncing quickly, or a background task crashing — and nothing happens.
Developers traced the issue to a bug in Shortcuts’ Calendar trigger mechanism on macOS. For some users, Calendar events were being monitored unreliably. Triggers didn’t fire consistently, especially if the event was recurring or located in a third-party synced calendar (like Google).
This was especially bad for people who relied on these for accessibility, reminders, or full-blown home automation.
Cries for Help
Automation fans did what any frustrated nerd does: they tested everything.
They:
- Reinstalled their Shortcuts
- Re-synced their calendars
- Created new test events with new triggers
- Moved events across calendars
For many, none of these worked.
This left the community itching for a fix. An update? A patch? Anything?
The Genius Workaround: Time-Based Triggers
While Calendar Triggers were misbehaving, Time-Based triggers were solid as ever.
So, developers and tinkerers started saying: Forget the calendar. Use the clock instead!
Instead of basing your Shortcut on when your calendar says “Morning Routine,” they said:
- Set a Time Trigger — For 7:00 AM
- Add conditional steps — Have the shortcut check if today is a weekday, if there’s a Morning tag, or even if a calendar event is scheduled
That workaround looked like this:
- Trigger the Shortcut at 7:00 AM
- Check if there’s a calendar event that matches “Morning Routine”
- If yes, run the rest of the automation
Smart, clean, and it worked.
Why This Works
Let’s get a bit techy (just a bit):
Time-based triggers don’t rely on syncing or calendar data. They are system-level Scheduled Jobs. These are sturdy and not affected by bugs in third-party services like syncing calendars or iCloud lag.
You can rely on them.
Calendar events, though? They need successful syncing, correct permissions, battery health, app state, and more. That’s a tall order for something to happen perfectly at 7:00 AM on the dot.
The Shortcut Community Comes Through
Automation experts began publishing fix videos. Posts went live with full guides like:
- “How to Replace Calendar Triggers with Time Triggers for Reliability”
- “Build a Conditional Morning Routine Based Only on the Clock”
Folks shared their modified workarounds. Some even improved their routines by adding extra smarts:
- Skip the routine if it’s the weekend
- Send a notification if the routine didn’t run
- Track skipped routines in a Numbers spreadsheet
If anything, the Calendar bug gave everyone a little boost in creativity.
Apple’s Quiet Response
So… did Apple acknowledge it?
Kind of.
No big blog post. No loud headlines. But after enough bug reports and developer feedback, minor macOS updates began improving Shortcuts reliability.
Eventually, Calendar triggers started working again for some users. But others still experienced issues — especially with third-party synced calendars like Google or Outlook.
That means the workaround stuck around. And probably will for a while.
How to Future-Proof Your Shortcuts
If this shook your confidence in automation, you’re not alone.
Here’s how to build your automations smarter now:
- Use Time-Based Triggers — More reliable than Calendar triggers
- Check Conditions — You can still reference your calendar from inside the shortcut
- Log Results — Add a notification or a line in Notes that confirms if your automation ran
- Test Often — Especially after updates
Bottom line: Your calendar can still inform your day, but the clock is your boss now.
Conclusion: A Bumpy Start to Better Automations
Sure, it was frustrating. A little broken calendar trigger messed up many people’s mornings. But it also led to better, cleaner, and more reliable solutions.
Turns out, letting the clock lead the way isn’t such a bad thing. Especially when it means your coffee is brewed right on time.
So here’s to speedy bug fixes, brilliant workarounds, and smoother mornings.
