Reminders app doesn't work with reminder notifications associated with Tasks created in 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.


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.


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:


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 4ish weeks after the task is due on the next instance of the Task recurrence.



After 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 then tried creating the new task in the Reminders app. 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 in Reminders a new instance is created. Unfortunately, if you mark the task as completed within Outlook it marks it as complete and them removes the task from Reminders completely.


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


If anyone has any suggestions, please let me know as I've tried all I can think of to troubleshoot this.

MacBook Pro 16″, macOS 11.6

Posted on Dec 1, 2021 12:46 PM

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Dec 2, 2021 9:23 AM in response to Sonicray

Hah. ITS at my university being helpful about something like this? We don’t have a mac support group; and our support system is super awful in general. As an example, they told us not to upgrade to Windows 11 or Big Sur because it didn’t work with some of their systems. Promised a progress update soon. That was over a month ago. Not even any mention of what systems so users could make the decision themselves. A follow up got the same response. I don’t think that is the issue here as it happens on my up to date iphone, but it will become as issue as apps update to using Big Sur. Anyway.


I don’t think it’s a setting on the Exchange server as there are a couple of reminders that work perfectly. And luckily those are the ones that recur most often so I’m not touching them. I don’t think I did anything different to create the ones that work and I can’t copy and paste a task in outlook (which is where I know I created the ones that work).

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Reminders app doesn't work with reminder notifications associated with Tasks created in Outlook

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