Recurring daily tasks that roll over / pile up when not completed

Hello all,

Apologies if the answer to this is out there. I read around pretty extensively and thought I found the solution, but it is not working.

The situation and need:
I have a fixed number of evaluations that must be completed in a given month. To ensure I meet my quota, I need to do at least two per workday. I am looking to set up recurring tasks for this purpose. These tasks need to pile up if they are not completed. For example, if I do not complete today’s evaluations, I need to have two past due tasks AND the two additional tasks waiting for me when I open OF tomorrow morning. If I slack off again, the third day would then have six total tasks: four past due, two due end of that day. And so on…

I tried to…

  • create 2 tasks titled “Eval” within a single-item project (project itself contains other items that need completed on a daily, weekly, monthly, or quarterly basis)
  • defer: today 6am
  • due date: today 2pm
  • repeat: every 1 week, MTWRF
  • repeat from: Assigned Dates

What happens: Only the tasks that remained incomplete from the previous day are present when opening OF in the morning. No additional tasks present. The new tasks seem to generate only when I mark the existing tasks as complete.

What am I doing wrong? Or am I looking for something that is not possible?

Thanks in advance to anyone who can or tries to help!


I don’t think you’re doing anything wrong, but you’re right that new tasks generate only when the existing tasks are marked as completed. There’s not really any getting around that. This will generate all the tasks you need, i.e. if you don’t complete Monday’s task until Wednesday, a new overdue task for Tuesday will be created, and if you don’t complete that until Thursday, you’ll get Wednesday’s task, and so on. But only one will show at a time. That might be okay, as long as you know that’s how it works. (You should know how behind you are based on the due date!)

I think if you really need this set up in the way you are describing and it repeats each month, you could consider creating two tasks for each day of the month (much like those you’ve already created) and have them repeat monthly.

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Thanks very much for your help. I suspected this was the case but wanted to confirm before I forge ahead with another solution. I know I can tell by the due date, but seeing them pile up is more of a motivator for me. This particular task is my least favorite aspect of my job and I need a real kick in the rear end sometimes to get going on them lol.

I think I’ll rig up an AppleScript on a cron job to add the tasks daily.

Thanks again for your help!


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I think @kaitlin is absolutely right. I would adopt the same approach, albeit I would probably do it on a weekly basis if I could, eg: Monday Eval 1 due at x time, Monday Eval 2 at x time as well.

Repeat from assigned date, but this could create difficulties if you get more than a week behind.

You should then see them pilling up in forecast.

FYI, I appreciate this is off topic, but you can achieve this much more easily with repeating tasks in Things 3. Might be overkill for this one thing though!

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Thank you for your suggestion! I will give things a go. While I love OF, perhaps Things is better suited to my needs.

Ya’ll rock! Appreciate the community support.

If I understand you correctly @derekcosta, then this should be a simple solution to address what you’re trying to do:

Create one task for each workday, with each of these tasks set to recur weekly on the respective workday. Now, if you don’t complete the tasks of the previous workday, on the next day they will be shown as overdue and, in addition, you will also be reminded of the tasks set to recur on the new workday.

Hope this helps.

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