How-to

How to Set Recurring Reminders That Don't Break

By Vyshakh Nair, Founder, Ultra Reminders · Updated May 9, 2026 · 8 min read
Part of the master guide: The Definitive Guide to Apple Reminders in 2026

Recurring reminders in Apple Reminders cover daily, weekly, monthly, yearly, and custom interval schedules but break on every-Nth-day, last-business-day, and nth-weekday patterns. Ultra Reminders adds the recurrence rules Apple has refused to ship for years, plus a fix for the documented "reminders reset to today" bug that has been live since 2022.

October 2025. Ravi noticed his "pay rent" reminder had quietly reset itself to today's date for the fourth month running. The recurrence said "1st of every month." It was the 14th. His rent was a week late. The rule was correct. The execution was broken. This is the story of recurring reminders in Apple's app.

If you've never hit this, congratulations. If you have, you're in the right place.

What you'll achieve

You'll know exactly which recurrence patterns Apple supports cleanly, which ones break, and the workarounds for the broken ones. You'll have a tested fix for the "reset to today" bug and a process for catching it before it bites you. By the end you'll have a recurring system you can actually trust.

What you'll need

  • iOS 26+ or macOS 26+ for the latest recurrence options (older versions support fewer patterns)
  • An iCloud account signed into Reminders
  • Optional: Shortcuts for the multi-rule workaround
  • Optional: Ultra Reminders if you want the patterns Apple won't add

Step 1: Set the basic patterns that work

Open a reminder. Tap the info button (the little 'i' or the details panel). Toggle "Repeat." Apple gives you these options out of the box and they all work reliably:

  • Daily. Every day. Use for habits.
  • Weekly. Every week on the same day. Use for weekly meetings, weekly reviews.
  • Biweekly. Every two weeks. Use for fortnightly check-ins, alternate weekend custody.
  • Monthly. Every month on the same date. Use for rent, bills, subscriptions.
  • Yearly. Every year. Use for birthdays, anniversaries, annual reviews.
  • Custom. Lets you set "every N days/weeks/months/years."

Custom is the underrated one. "Every 3 days" works. "Every 2 weeks on Tuesday" works. "Every 6 months" works. Set these and they hold.

The end-repeat option lets you cap the recurrence ("repeat every Friday until December 31"). Use this for time-bounded projects.

Step 2: Identify the patterns that break

Here's the honest list of what does NOT work cleanly in Apple Reminders as of May 2026:

  • Every Nth weekday of the month (last Friday, first Monday, third Tuesday). Apple does not have this. You can fake it with "Monthly on Friday" but you'll get every Friday.
  • Last business day of the month. Not supported. End-of-month varies between 28th, 30th, 31st, plus weekends.
  • Every weekday except Wednesday. No "skip days" pattern.
  • Every other Tuesday. Sort of works via "Biweekly" if your start date is a Tuesday, but breaks if you accidentally edit the start date later.
  • Hourly. Disappeared on iPhone in some iOS versions. See The Hourly Reminders Disappeared Problem on iPhone for the current state.
  • Conditional recurrence ("repeat only if previous was completed"). Doesn't exist.

"I needed a 'last business day' reminder for our month-end close. Spent two hours trying to fake it in Reminders. Eventually built a Shortcut. Eventually gave up and moved to a third-party app."

  • paraphrased from r/macapps, February 2026

Step 3: Workaround for "every Nth weekday"

You want "first Monday of the month." Apple won't give you this directly. Workaround:

  1. Build a Shortcut named "Schedule First Monday Reminder"
  2. Action: Get Today's Date
  3. Action: Format Date to first Monday of next month using the formula (figure out next month's 1st, then add days until you hit Monday)
  4. Action: Create Reminder with that date
  5. Schedule the Shortcut to run on the 1st of every month via Personal Automation in Shortcuts

The Shortcut creates a single dated reminder each month. It's not a true recurrence; it's a scheduled creation. Functionally identical for your purposes.

Same approach works for "last business day": Shortcut runs on the 28th of every month, calculates the last weekday of that month, creates a reminder for that date.

Step 4: Fix the "reset to today" bug

This is the one that costs people money. The pattern: a recurring reminder ("Pay rent on the 1st") silently resets its date to today, then re-completes on whatever today is. Result: you think you're paying rent on time. You're not.

The bug has been documented since 2022 and is still present in iOS 26.1 as of May 2026. Apple has not committed to a fix.

Diagnostic process:

  1. Open the reminder
  2. Check the date shown
  3. If the date matches "today" but the recurrence rule says "1st of month," you're hit
  4. Check completion history (long-press the reminder if available)
  5. If you see multiple completions on consecutive days when the rule is monthly, confirmed bug

Workarounds, in order of reliability:

  • Don't mark it complete on the iPhone. Mark complete only on Mac. The bug fires more often on iPhone, less often on Mac.
  • Set a calendar event in parallel. A real Calendar event with an alert, in addition to the reminder. The event is your safety net.
  • Use a dedicated app. Ultra Reminders catches recurring rules and re-emits them deterministically, so the reset doesn't happen on its layer.

For the deep-dive on this specific bug: Why Recurring Reminders Reset to Today.

Step 5: Test your recurring rule before relying on it

Before you trust a recurring reminder for something important (rent, taxes, medication), test it.

  1. Set the recurrence to start "tomorrow" with whatever pattern
  2. Wait for tomorrow
  3. Mark complete
  4. Check the next instance: did it advance correctly per the rule?
  5. Repeat for 2-3 cycles

If it survives 3 cycles cleanly, you can probably trust it. If any cycle resets to today instead of advancing per rule, do not use Reminders for this. Use Calendar.

"After my second missed mortgage payment because the 'every month on the 1st' reminder rolled to today, I just put it in my Calendar instead. Calendar doesn't reset itself."

  • paraphrased from a Hacker News thread, October 2025

Step 6: Handle subtasks under recurring tasks

Subtasks under a recurring parent do NOT respect the parent's recurrence. When the parent recurs, the subtasks come along but they don't reset to incomplete. They stay completed from the last cycle, which makes them invisible until you uncheck them all.

Workarounds:

  • Don't use subtasks under recurring parents. Flatten the subtasks into separate recurring tasks if you need them to recur.
  • Manually uncheck before each cycle. Brutal, but works.
  • Use a Shortcut. Run a Shortcut that finds completed subtasks of a specific recurring parent and unchecks them all. Schedule daily.

For more on the subtask problem: How to Create Subtasks and Sublists in Apple Reminders and Why Your Reminder Marks Itself Incomplete.

Step 7: Use Ultra Reminders for the rules Apple won't ship

Ultra Reminders adds these patterns natively:

  • Every Nth weekday of the month
  • Last business day
  • First/Last working day, accounting for holidays
  • Every weekday except specified days
  • Every Nth day with start anchor
  • Hourly with custom interval and escalation alarm
  • Conditional ("repeat only if previous completed")

The rules are stored in Ultra Reminders' local layer and synced back to Apple Reminders as one-off date stamps when applicable. So your iPhone, iPad, and Watch still see the right reminder; the rule complexity lives in the Mac app.

Setup: open Ultra Reminders, create a new reminder, choose "Advanced Recurrence" from the recurrence dropdown, build the rule. The app generates the next 12 instances and writes them to iCloud. As you complete them, more get generated.

Common pitfalls

  • Editing the start date breaks the recurrence anchor. If you set "every other Tuesday" starting Tuesday, then edit the start to Wednesday, you'll get every other Wednesday or weird offset behaviour. Don't edit start dates on recurring tasks; delete and recreate.
  • Time zones reset on travel. A recurring 7am reminder set in Bangalore becomes 7am New York time when you land in New York. Set the time zone explicitly via the time zone field in the reminder details.
  • Completed instances pile up. A daily reminder run for a year is 365 completed entries. Some smart lists count these. Consider archiving completed lists periodically.
  • Skipping a cycle by completing twice in a day. If you complete a daily reminder twice on the same day (once on Mac, once on iPhone), the second completion can advance the date by two days instead of one.
  • Custom intervals over 999. Apple caps custom intervals at 999 of the chosen unit. "Every 1000 days" silently fails.

Verification

Your recurring reminders are working correctly if:

  1. Each completion advances to the next correct instance per the rule
  2. The displayed next-due date matches what the rule would calculate by hand
  3. iPhone, iPad, Mac all show the same next-due date
  4. The reminder fires its notification on the new date

Your recurring reminders are broken if:

  1. The next-due date is "today" when the rule says otherwise (reset bug)
  2. The recurrence skips a cycle silently
  3. Subtasks remain completed across cycles
  4. The notification doesn't fire on the next-due date

When verification fails, see Apple Reminders Notifications Not Working: Complete Fix List for the notification side, and consider whether you've outgrown the native app's recurrence engine.

For the broader limitations picture: 13 Apple Reminders Limitations Power Users Hit.

FAQ

Q: Why does my recurring reminder reset to today?

A: Documented bug, present since 2022, still in iOS 26.1 as of May 2026. Most reliable workaround is to mark complete only on Mac, not iPhone, and to set a parallel Calendar event as a safety net for anything time-critical.

Q: Can I make a reminder recur every other Wednesday?

A: Yes, via Custom recurrence: every 2 weeks, on Wednesday. The biweekly preset also works if your start date is a Wednesday. Don't change the start date later or the cadence will drift.

Q: How do I set a reminder for the last Friday of every month?

A: Apple Reminders does not support this natively. Workarounds: (1) Build a Shortcut that runs on the 25th of each month and calculates the last Friday, then creates a one-off reminder. (2) Use a third-party app like Ultra Reminders that supports nth-weekday rules natively.

Q: Do recurring reminders work on Apple Watch?

A: Yes. The Watch surfaces the next instance and lets you complete it. Completion syncs back to iCloud. The same reset-to-today bug can fire from a Watch completion, so the Mac-only-completion workaround applies if you've been hit.

Q: What's the highest custom interval Reminders supports?

A: 999 of the chosen unit (days, weeks, months, years). "Every 1000 days" silently fails to set. If you need very long intervals, use a yearly recurrence and adjust the date by hand each cycle.

Ultra Reminders solves smart recurring rules Apple has refused to ship for years. Free 14-day trial at ultrareminders.com.