Reminders app doesn't handle recurrence of "first weekday of each month" from Outlook

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Reminders app doesn't handle recurrence of "first weekday of each month" from Outlook

I think this may be a bug, but thought I'd ask here first.

I use Microsoft Outlook for Mac (v 16.55 with an Office 365 subscription) and use the Exchange server at work (a university). I have a variety of reminders for things that need to be done on different schedules. A couple of those things are tasks that need to be completed on the first workday of every month. I can create this task in Outlook with no problem. But my Reminders app (both on Macbook Pro 16" running Big Sur 11.6 and my iPhone 13 pro running iOS 15.1) gets the first instance just fine, but changes first weekday to first Monday. Then, when I mark the task as completed (in Outlook or the Reminders app), things go more wrong. When I mark it as complete in Outlook it looks like it works just fine; however, when the info gets synced to Reminders, the task is reprogrammed (for lack of a better word) to be the first Monday of the month AND it sets the reminder notification to be a random day that is after the actual task due date. This is repeatable and I've included some screen shots to help explain what I mean. When I look at the task info in Reminders I can see that the repeat option is set to "Custom" with no way to look into it further, so I think this is a problem with Reminders at its core but wanted to reach out and see if anyone had any suggestions.

If it's relevant, I have NOT updated Outlook to the "New Outlook" specifically because when I was first prompted to do so it messed up tasks. I'm not sure if that has been fixed and it would help, but I also don't want to lose my tasks so am wary. And I also can't upgrade to the new OS as my university has identified some issues with it and their systems, but this happens in the latest version of iOS so shouldn't be that.

My task as I create it in Outlook:

Task in Outlook after creation

Task in Reminders app after creation - note change to first Monday:

The Outlook task retains the correct recurrence, and even updates to the next instance correctly:

After syncing between Reminders app and Outlook, the task (and reminder notification) is now messed up:

MacBook Pro 16″, macOS 11.6

Posted on Dec 1, 2021 11:32 AM

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Answer 1

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LeaMedeiros Author

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Dec 1, 2021 12:37 PM in response to LeaMedeiros

UPDATE: This isn't a good work around... if you mark the task as completed within Outlook it marks it as complete and them removes the task from Reminders completely.

=======================

Well, turns out I was doing it the "wrong" way. I think it should work either way, but I believe the issue stems from the problem that the Reminders app uses the date field for both the due date and the reminder (considering them to be the same thing), whereas Outlook will remind you prior to the due date.

Creating the new reminder in the Reminders app lets me specify everything I want (even the first weekday of each month), sends me a notification, and syncs with Outlook. The task in outlook is NOT a recurring one, but when I mark it as complete a new instance is created.

Even if this isn't how things "should" work, it's a valid work around considering the date field limitation in Reminders.

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Answer 2

LeaMedeiros Author

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Dec 1, 2021 11:39 AM in response to LeaMedeiros

Updated to add that, even if I try to work with the Reminders app and set the Outlook task to be the first Monday of every month, the reminder notification still gets set to 4 weeks after the task is due on the next instance of the Task recurrence.

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Answer 3

LeaMedeiros Author

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Dec 1, 2021 11:58 AM in response to LeaMedeiros

Updated (again) to add that I tried setting the recurrence to be a particular day of the month (the 1st) and the reminder notification was once again pushed back on the next instance of the Task.

Then I tried leaving the reminder notification off of the task and next instance due date (in Reminders) appears ok, but I wasn't sent a notification (even though the info in the Reminder app has the box for "remind me on a day" checked).

I guess it means it's an issue with the reminder notification itself? Super frustrating.

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Answer 4

LeaMedeiros Author

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4 points

Dec 1, 2021 12:34 PM in response to LeaMedeiros

I will add that I do have some Tasks that seem to work just fine and as expected. They are weekly reminders, but as far as I can tell that's the only difference. I don't know why they're different, but I'm not messing with them.

And, as an FYI, the new Outlook still doesn't have Tasks working.

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Reminders app doesn't handle recurrence of "first weekday of each month" from Outlook

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