Apple

Apple Needs To Do Some Serious Work With iCloud

iCloud OS: Apple’s Unnamed Operating System. The second in a series heading into Apple’s WWDC 2024.

WWDC is designed to highlight future directions for Apple’s increasing number of operating systems and how they work together. The OS list is long and getting longer, but there’s actually one that Apple has never mentioned as an operating system, yet it’s the one that glues every other piece of the ecosystem together. I call it iCloudOS. Like any glue it can fasten and bind, but apply it without care and you can end up with a sticky mess. iCloudOS is a bit of both.

If you use multiple Apple devices iCloud ties them all together creating a supposedly fluid connection between devices and services. That’s the attraction of the ecosystem. When it works as designed it can feel magical. Copy and paste between devices, universal control, handoff, shared Notes and Reminders and others all make Apple computing life more productive and often more fun.

When things don’t work it reminds every parent of raising a child. There are moments of sheer wonder and joy, but you know at some point the kid is going to shit the bed. There’s too much of the latter to ignore.

I’ve written extensively about my iCloud woes (here, here, here, here, and here). I’ve had numerous conversations with Apple tech support personnel. What I’ve discovered is that there are ongoing iCloud backend issues that Apple hasn’t been able to solve. They keep trying, but they keep getting put on the back burner once Apple gears up to roll out its next big new thing, as is the case with this year’s now well predicted AI announcement. Things reach a point when a “wait until next year” mandate takes hold that would test even a Chicago Cubs fan’s patience.

In my most recent adventures into the backend of iCloudOS it has been acknowledged that all of the work we were doing to pin down the issues I and others have been seeing has been put on hold until after whatever is coming next in the various operating systems due to be announced next week. All well and good, I suppose, but here’s the problem with that. That approach essentially makes all users of the ecosystem beta testers. I do not run betas on my devices but I’ll suffer through the numerous summer releases and whatever changes Apple makes on the backend during the summer beta season. That will continue with each point release throughout the year. Keep in mind, we’re all, always at the mercy of the backend.

I’ve already seen this begin to happen and the betas don’t roll out for a week or so yet. One of the early warning signs(and there are quite a few) that things are happening in iCloudOS is when notifications for Apple’s Reminders app get out of sync between my macOS devices and iOS devices.

Remind Apple To Fix This iCloudOS Problem

As an example my wife and I share a Reminders list for grocery shopping. I’ll often do the shopping and dutifully check off each item on the list once it’s in the grocery cart. This will sync accurately among my iOS devices as designed, but when Apple is noodling around on the backend, the Reminders notifications will linger on the Macs long after I’ve returned home and put the groceries away. The only way to remove them is to open the Reminders app and wait a few minutes for the sync to catch up.

Apple’s iCloud has gotten so much better since its initial debut, but these problems remain and keep getting put off year after year. Most notably, users aren’t freely allowed any control over syncing when things appear stuck. The Reminders issue I spoke of above doesn’t happen all the time. But it happens regularly enough ahead of Apple releasing new beta or OS releases to serve as a signal that changes are coming down the pike. It creates a situation that removes trust between the user, the devices and the ecosystem.

There’s A Difference Between macOS and iOS

One of the things I’ve learned in my digging and Apple Support conversations is that these iCloudOS issues affect iOS and macOS differently. They may be connected at the hip but they are not necessarily walking in step. In my case typically all things work fine and as advertised between my iOS devices. I can’t recall an issue with those devices.

Connect a Mac to the chain and the sync can, and too often, goes sideways. It happens with Apple’s own apps including Reminders, Photos, Notes, Messages, Contacts and Mail. There have been numerous calls for “Sync Now” buttons to appear in some of these apps to no avail. It’s almost as if Apple is afraid of breaking things more than helping users enjoy what it purports to offer.

I came closer to nailing this down after my wife and I recently moved. Both of my Macs were packed away for a good portion of the move and I was using my iPhone and iPads while we were in the final throes of taking our living quarters from one place to the other. All iCloud features worked as advertised between my iOS and iPadOS devices. Once I began setting up my new office, on a new network, the problems resurfaced on the Macs. Note that new point release versions of the operating systems were released while we were moving.

The issues also surface differently on an M1 iMac24 and an M2 MacBook Air. They happen more frequently on the iMac, but when they do appear on the MacBook Air, the workaround to fix things happens more quickly. That workaround is to sign out of Messages in iCloud and sign back in. On the iMac24 the workaround also additionally requires a reboot. It rarely does on the MacBook Air. Each time I perform that workaround I receive a notification that a new Mac has been added to my iCloud account. I stopped taking screenshots of those notifications quite some time ago because they appeared so frequently.

I’m reminded of a time back in the day when Robert Scoble was taken to task because he argued that Windows machine users shouldn’t complain about having to reboot their devices each day. These issues with Apple’s ICloudOS don’t require a daily reboot, but they happen frequently enough to make one day blur into another during beta cycles.

Apple’s ecosystem that I’m calling iCloudOS is one of the selling points. But it contains eco-unfriendly failure points that can too easily be shunt aside in the rush to push something new and shiny into the marketplace. I think that’s more apparent now that Apple is in a rush to catch up with AI. Regardless of what and how Apple rolls out its “keep up with the Joneses” AI initiatives a new layer of complexity is about to be rolled into iCloudOS. Each year Apple needs something new to keep and attract users and like it or not, AI is that something new this year.

Apple may have to go down this road, but Apple’s iCloudOS reminds me very much of how the city of Chicago, where I live, treats the inevitable potholes that crop up every winter. They patch and fill them in and they inevitably appear again with regular use. Only rarely does the city do the infrastructure work and repaving necessary to fix the underlying issues. And woe be unto you if you live in a ward not heavily trafficked. You become like one of those “small minority of users” Apple is so fond of defending itself with. In my opinion, Apple needs to do some serious roadwork with iCloudOS and its ecosystem.

This is the second in a series of articles heading into Apple’s WWDC 2024. The first can be found here.

You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome. I can also be found on social media under my name as above.