Reminders stop synching Apple Watch / iPhone

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AFG

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I was starting to depend on Apple's Reminders on my watch as a way of doing GTD on-the-fly capture. E.g. while walking dog, hands full leash/bag, I could say "Hey Siri", and capture items for later review. Great for groceries; pretty good for work ideas.

This worked for circa a month.

I was beginning to think about making Reminders my main GTD list manager. ...

However, with recent iOS/WatchOS updates, both Reminders and Calendar stopped synching between my Apple Watch and iPhone. No success fixing, neither reading support articles at Apple or oter websites, not Apple support phone, not Genius Bar. I have escalated from "Reset Synch State" to resetting entire watch, in combination with restoring iPhone from an iCloud backup. I have not yet tried reinstalling iPhone from scratch, but that is next escalation. In meantime, I am waiting for Godot, sorry, waiting for Apple to release a bug fix, etc.

Calendar was the main reason I bought my Apple Watch - no that's just wasted money and time.

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As part of this debug I made a non-Apple backup of my iCloud Reminders - since one of the recommended steps was to delete existing Reminders lists ad To Do items.

In case anyone else has to do this:

The only way I found to Export my Reminders was in the Reminders app on MacOS. (I nolonger have a MacBook, borrowed my daughters.) Exports to a.ICS file, which is an easy to parse text format: VTODO: etc.

There appears to be no way to Export Reminders
  • on iCloud website
  • on iPhone
  • on iPad (older)
I tried installing the iCloud app on my Windows PC, but install failed.

MORAL: before you get dependent on a tool, verify that there is a convenient way to export to a non-proprietary format.

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Posting this because

a) slight chance somebody here may know fix

b) to warn others not to depend on Apple Watch Reminders in your GTD system

and perhaps to ask people how they deal with potentially unreliable software.

I would prefer to completely avoid unreliable software. But, Reminders was reliable in old WatchOS/iOS; it appears likely the "upgrade" introduced the bugs.
 
I experienced a hiccup with iOS 12 and WatchOS 5. My calendar stopped syncing to my watch, but the second “Reset sync state” did the trick. Usually these things resolve fairly quickly. You can have problems with any upgrade. I think Apple is as good as anybody at hardware and software, but the environment we live in now is quite complicated. Just a few years ago nobody could reliably sync much of anything.

There is another way to export calendars that may not be obvious: you can subscribe to your calendars with another program, say goal, and, e.g., make duplicates.
 
mcogilvie said:
I experienced a hiccup with iOS 12 and WatchOS 5. My calendar stopped syncing to my watch, but the second “Reset sync state” did the trick. Usually these things resolve fairly quickly. You can have problems with any upgrade. I think Apple is as good as anybody at hardware and software, but the environment we live in now is quite complicated. Just a few years ago nobody could reliably sync much of anything.
Click to expand...

Thanks for holding out hope.

I have "Reset Synch State" 3 times, "Erase Apple Watch Content and Settings" 3 times, Unpaired 4 times, in combination with several iPhone resets and at least 3 iPhone restores from backup. Uninstalling/reinstalling the Reminders app. Unfortunately can't restore to pre iOS 12.

Interesting: after I do one of these reset watch/restore iPhones, I briefly saw Calendar and Reminder synching - but then it failed, and all synched items disappeared from watch. Which implies it is a problem with data cached in iCloud, dates, etc.

Only likely thing I haven't done is reinstall all from scratch. But that takes days to fix things up. Apple Genius Bar recommends connecting as a different iCloud user, in the hopes that will flush any caches involved.

There is another way to export calendars that may not be obvious: you can subscribe to your calendars with another program, say goal, and, e.g., make duplicates.
Click to expand...

I tried several such programs, finding no export feature. I will add Goal to my list to try.

I have started using IFTTT rules to make copies of new Reminders to OneNote, but IFTTT's security scares me.
 
I once spent forever trying to figure out why syncing was intermittently failing for Reminders between my phone and my laptop, and discovered that I had turned off Reminders' ability to use cellular data on my phone. Probably not that, but just in case.
 
ssksogaard said:
Have you tried to delete/restore the iWatch (remember to unpair iWatch and iPhone first) just to set i up from scratch?
Click to expand...

Yes. I also got the Apple Store Genius Bar guy do the same, in case I had done it incorrectly.

Still stuck Oct 17, after problem occurred circa Oct 7.

Other symptoms:

If I create a new List in Reminders\iPhone, and then do various Watch resets, such as "Reset Sync Data" in iPhone Watch app, I eventually see the new List on my Watch. But not any of the items within the List.

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Hypothesis: I wondered if some other app that had access to Reminders was messing up timestamps. E.g. the IFTTT app I started using after the first time I noticed this problem, to "back up" reminders automatically. E.g. a calendar app like Fantastical. I have disabled all such apps that I am aware of. Problem persists.

Q: is there a way to find all apps, whether iPhone, Watch, Mac, or other ()e.g. accessing via iCloud) that have access to my Calendar and Reminders? I would like to disable all such access, excet for the standard Apple Calendar and Reminders.

BTW - although Calendar and Reminders supposedly go together, frequently I can see Calendar items on my Watch, but never Reminders. Although just now I opened Calendar\Watch, briefly saw my Calendar, and then had everything disappear. Once or twice I saw sometyhing similar in Reminders\Watch. So the problem may be affecting both Calendar and Reminder.
 
Gardener said:
I once spent forever trying to figure out why syncing was intermittently failing for Reminders between my phone and my laptop, and discovered that I had turned off Reminders' ability to use cellular data on my phone. Probably not that, but just in case.
Click to expand...

Thanks. Checked. Not the problem.

In fact, if anything I have seen the opposite - no syncing when in an area with no cell coverage, just wifi; get to cell coverage, BRIEFLY I see Reminder and Calendar, but then they are emptied.
 
Have you tried forcing a sync from the iCloud website in a browser? Some time ago I had issues with Calendar items not syncing across multiple devices. After trying various ways to get things to sync I went to the iCloud website and unticked all calendars on the left of the Calendar main page, left it for about 10 minutes and then ticked all the calendars again. Everything then started syncing without issue. I don't know about Reminders as I don't use them, but maybe just kicking things directly at the main iCloud webpage might force a new sync directly from Apple's servers.
 
Finally, more than 2 weeks later, I have Reminders synching Watch<->iPhone again.

I eventually did a full factory reset and install as new watch.

iOS 12.0.1
Watch 5.0.1

Install as new watch takes many hours, days, to recover from. :-(

--

Nov 5: still running into things that I need to reinstall/reconfigure since my factory reset/install as new.
 
Last edited:
I am happy to report that

not only are Reminders synching Watch<->iPhone

but the new-ish version of Reminders on my Watch allows me to designate most of the standard GTD lists by name:

"Hey Siri, add item to my Agendas list"
etc.
 
AFG said:
MORAL: before you get dependent on a tool, verify that there is a convenient way to export to a non-proprietary format.
Click to expand...
Well said. As more of our assets become data in a program, end-of-life issues and data exporting must be considered. For decades I used Home & Business financial management software. I went with their cloud-based version, exported all my data to it and then they discontinued this cloud service to focus on a free version (where the biz model is to sell users data). There was no way for me to migrate my data out.
 
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