Reminders can't sync, reliably, between Mac and iOS

Originator:piet
Number:rdar://25640649 Date Originated:09-Apr-2016 10:44 AM
Status:Open Resolved:
Product:Other Product Version:10.11.4
Classification:Serious Bug Reproducible:Always
 
Summary:
Use glorious Apple devices to setup a shared reminders list, be excited how well this seems to work, fall into a pit of despair when things stop working in mysterious ways.

Steps to Reproduce:
Setup: 2 iPhones and 1 mac that share a Reminders list (1 apple account for iPhone and Mac, 1 apple account for other iPhone)
Throughout the week enter items from iOS devices to the shared reminders list
Saturday morning open that list on Mac to edit it so you have an ordered shopping list.

Expected Results:
The Mac reminders list is up to date and sorted like on the iPhone.
After editing on the mac, the iPhones reflect the state the Mac is in.

Actual Results:
The Mac is:
- sometimes not in sync with the iPhones
- editing on the Mac is not reflected on the iPhones
- some items are duplicated while editing on the Mac

Regression:
Before 10.11.4 and 9.3, this was working somewhat reliably, with the one caveat that sorting wasn't synced from Mac back to phones, I worked around this by manually (or rather Apple scripting) adding the items on the mac in the order that I wanted.

Notes:
It's a shared shopping list, so at the moment it has 406 Completed items, we use the phones throughout the week to add items to the list; the iPhone is surprisingly adept at small task while on the go!; in the weekend I like to go over that list and put it in order, add items etc. on the mac; the Mac is surprisingly adept at editing and processing information while stationary!.

This does mean that the list ends up to be around 40 items, and gets edited rather heavily (items added, reorderd etc.) maybe this messes up the sync?

I've disabled iCloud on the Mac, then reenabled it, this seemed to solve it somewhat, as throughout the week it appeared to be back in sync. However, I opened Reminders this morning and it was showing my shopping list from last week (which was completed) and at the bottom some of the items that were added throughout the week.

The iPhones only showed (all) the items that were added throughout the week. Now I can't seem to figure out any way to reliably get them back into sync, yay the future of computering!

(As a workaround, I managed to get most of the items out of it, pasted them into Emacs (thanks for being able to copy items to plain text), formattted them correctly, opened OmniFocus and pasted them there. OmniFocus then made a list of items out of each newline (copy that, it's just great) and synced it using WebDAV to my iPhone.)

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