Apple Notes and iCloud Syncing: Breaking a Good Thing Badly

“Random is always righter” a scenic designer colleague of mine was fond of saying. A saying that I happen to agree with when creating magic for the stage. Forget that when it applies to the tools and technology I use to do my job as a theatre director and writer. Those tools of choice are Apple products. MacBooks, iMacs, iPhones, iPads, Apple Watches, etc.. etc.. I have used them and continue to use them because I like them. Apple’s hardware is often stunning and high powered, making it easy for me to justify the high prices. Set aside the hardware though, because I also use Apple’s software and services to connect these devices and share data. That’s a different story. With a rampaging randomness that keeps increasing with each new generation of operating systems and “improvements”, Apple seems to be connecting it’s excellent hardware with a cloud system that can best be described as fog bound.

Apple Notes is my focus here, because it’s the latest, most egregious example of how Apple just can’t get things right on its backend, creating an unusable situation for those who want to use Apple’s software. I’m not alone with this complaint. I’ve heard it expressed on podcasts, most vocally by MacStoriesFederico Viticci, and seen similar complaints on Twitter.

Let me define my workflow. The major components include taking and making notes, gathering research, and writing. Over a 41 year career I’ve moved from legal pads and file folders to the digital world, first back in the days of the original Microsoft Tablet PC. Then gradually migrating to Apple products over the last 13 years or so. On both platforms I’ve used more note-taking and research gathering tools than I can remember. Name one and I’ve used it. Within the last several years I have settled on Apple Notes as my tool of choice, once Apple improved the product to a point that it could compete with other solutions.

Currently my workflow consists of morning work at either a MacBook Pro or an iMac; writing, reviewing and sorting notes from the previous day’s work, or gathering research, depending on what phase of the production process I’m in. I prefer the MacBook or iMac for this kind of morning work because it’s easier to multi-task. Once I leave the morning and head out for the day I take the iPad Pro 11-inch and the iPhone, currently an iPhone Pro 11. The iPad Pro is for work at the rehearsal space or theatre. The iPhone Pro is for capturing quick notes of inspiration along the way or when I’m out and about on other tasks. My note taking in general is an “always on” kind of process. I’ll start a note or a list and throughout the course of the day I’ll add to it or amend it as I mull things over. Frequently before I’m heading out for the day, I’ll find myself at the keyboard quickly organizing thoughts already jotted down, or making a quick note.

The simple idea is that regardless of where I am or when I choose to open up a device to see or make/edit a note, those notes are always available.

That’s not the case currently and the randomness is beyond maddening.

Recently, (and I sadly can’t pin this on recent iOS or Mac OS system updates because I just wasn’t paying close enough attention), I’ll create a note on one device and it may indeed show up on all three, or perhaps two, and sometimes it won’t sync off of the device it was created on until some random time down the road.

The behavior I was accustomed to was an almost instantaneous sync. In fact there were times when I’d be working on one device creating or making edits and I’d literally see the work I was doing on the original device appear almost in real time on another device’s screen if it was open. Magic.

Magic ain’t right if it’s random.

This syncing issue reared its ugly head after I arrived in Memphis for a five week gig directing a production of Peter Pan. I had spent a morning creating a number of notes on the MacBook in preparation for a production meeting. I walked to theatre, opened up the iPad Pro and none of those notes appeared. I checked the iPhone and some of those notes appeared.

Moving on, I created a few notes during that meeting on the iPad using the Apple Pencil. On returning back to the MacBook, those Ink notes didn’t sync over. The same was true on the iPhone.

So I began troubleshooting, creating notes on each of the three devices, checking to see what synced and what didn’t. I also created test notes on and checked to see if they synced. At the end of that testing period I ended up with four different note counts on three devices and the web. That’s not entirely accurate. The web view inexplicably doesn’t provide a note count. Suffice it to say that there were different notes in different places.

Further, it appeared that some of the notes, not all, I created that morning were gone from all devices and the web.

The next day I tweeted out my frustration and an Apple employee got in touch and we DM’d back and forth, eventually setting up what would be the first support call with a Senior Advisor. That first advisor seemed to think the issue was with the MacBook. Saying he was an iOS Senior Advisor he connected me up with someone who dealt primarily with Mac OS. I granted that advisor permission to take over my screens and we went back and forth creating notes on the different devices and he got to see first hand just how random the syncing issues were. He promised to escalate the issues to the engineering team and we set up a time to talk on my next day off the following week.

Something went awry, and that call never came, but I eventually got connected with another Senior Advisor later that day. We followed some of the same procedures and she determined that the next step would be to reset my iCloud database holding my data. She advised that I stay away from Notes as this reset would take 24 hours to accomplish.

I took her advice and actually stayed away from anything iCloud for two days. Taking a deep breath, I opened up Notes on each device and within a few minutes I was seeing the same notes on all three devices and each shared the same note count. The lost notes did not re-appear. Intriguingly both before and after this reset, what she was able to see was a larger number of notes than I could see on any device, a discrepancy of about 18 notes.

I proceeded to create new notes on all three devices and these new notes synced to all three devices. Some would do so in almost real time, harkening back to the almost simultaneous behavior I mentioned earlier. While the timing of the syncing still appeared to be random, it was within what I considered to be a tolerable time frame: a few minutes or so. The fact that notes synced was actually a big step forward. The things we settle for.

I worked this way for a day or so and reported on a follow up call from that Senior Advisor that things seemed to be corrected, even with the occasional random syncing timing.

Then this morning happened. I created several notes on the MacBook Pro prepping for tonight’s rehearsal. About 30 minutes or so later I opened up the iPad Pro to check on a note I’d written and it didn’t appear. With a sinking feeling in my stomach I opened up Notes on the iPhone. Not there yet either.

I waited things out and it was obvious those notes were not syncing within an acceptable time frame. But during that wait, on the MacBook Pro I captured some links on the web for items to add to my Christmas list in Notes. Those notes synced almost simultaneously to all three devices, but the notes I created earlier still had not.

Frustrated I prepared to recreate the notes on the iPad so I would have them in rehearsal, but I decided to see what would happen if I used Air Drop between the devices to transfer the notes. Those notes did indeed transfer to the Notes app on each device, although without the folder assignments originally created on the MacBook.

Still concerned, but satisfied that I had the data I needed for rehearsal, I put away the devices and attended to some other chores. When I returned to do some work later in the morning I took a look to see if any progress had been made.

Yes but mostly no.

Each device had a different note count. The MacBook had three copies of the same note, two in the proper folder, one not. The iPad Pro had only the copy that had been Air Dropped. The iPhone Pro had two copies. Edits made to another note on the MacBook earlier in the morning had not synced to either of the two other devices.

That’s where things sit at the moment.

“Random my be righter” in creating art, but that’s not the case when using any kind of technology to help you do so. Reliability and consistency should be the keys here. With Apple and its iCloud syncing woes I just can’t apply those labels with any reliability or consistency. Unless I apply them to say that Apple’s iCloud service is reliably and consistently not worth the trust Apple implies in its sales pitches.

Look I get it. These are big complex systems and sometimes things need to be worked out. So, I’ll grant some leeway for that. But I also get this. Apple has more resources at its disposal than most other companies and it needs to figure this stuff out. It should be embarrassing, but apparently it isn’t embarrassing enough to martial enough of those resources to fix iCloud, which is a system that Apple is relying on more and more as the backbone for services that connect these devices.

A recent TidBits article by former Apple Engineer David Shayer discussed how Apple prioritizes fixing bugs and problems. Something tells me that this iCloud syncing issue I and others are experiencing must fall into one of those, what I’ll politely call “shoved under the rug” categories. We’ve all heard Apple tell us when issues crop up that they affect a small percentage of users. That’s probably true. But when you’re that user, with a problem that Apple’s Senior Advisors, who promise to solve your problem, seem perplexed by, the problem is 100% yours.

I’ve got two suggestions for Apple on this.

  • You’ve got Mac and iOS Senior Advisors, perhaps you should also create positions for those who specialize in iCloud issues.
  • Give these applications a “Sync Now” button.

I’ve sent follow up emails to the Senior Advisor. To be honest, I don’t expect this to be resolved anytime soon. I’ll be re-exploring other options I’ve used and moved on from in the past. I’ve got work to do.

So does Apple.

UPDATE: The situation has gotten worse and the random behavior is beyond my comprehension. One note from last night’s rehearsal synced over properly, but several notes from earlier in the day did not, and others show up as duplicates on one device, not at all on another.

Apple support call scheduled for Monday.

UPDATE: Apple apparently has no clue on how to solve this issue. The problem has once again been sent to the engineers.

Theatre Guy, director, playwright, and mobile geek.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store