Dear Santa Tim Cook,
I’m writing you to let you know what I would like from Apple for this Christmas. It’s not new hardware. The amount of Apple gear I own is more than enough and I’m quite happy with it. So thank you for that, and thanks ahead of time because I’m sure Apple’s vision is to keep cranking out new hardware in the future.

This is a wish list about a number of nagging things that I think you and your elves need to pay more attention to in your operating systems and software. Let’s call them fixes. Most of these nagging issues have been around for a while and oft-reported so it’s surprising you’d allow them to hang around for the users who love your products. I, and many others, have been reminding you of them quite frequently and for quite a while.
I know your elves are busy, but if they could find some time to address these things it would be one of those gifts that gives all year long, and for years to come.
So, here’s my wish list for iOS and macOS.
iCloud
This is the big ticket item on my wish list. You’ve tied so many services and functionality to iCloud and a user’s AppleID. That makes good sense for the eco-system and when it works it’s great. When it doesn’t it causes problems for users, your support personnel, and completely diminishes much of the good it intends to provide. I’ve been on the hunt for solutions to my iCloud woes for quite some time now. I won’t go into detail here, but you can follow the links in this article that chronicle my journey.
But just so you know, the issues aren’t resolved, aren’t closed to being resolved, and tend to pop up with some sort of Santa-like omniscience, knowing when we users can least afford a problem.
Your elves I’ve spoken with thought this had been resolved with Sonoma and were quite disappointed to find out that wasn’t the case. So they’re as perplexed as your users.
These iCloud issues affect features like Handoff/Continuity and Sign in with Apple Watch not working. They also include Photos not syncing, Shortcuts not syncing, Mail not syncing, Reminders not syncing, iMessages not syncing, and the list goes on. To be fair, Photos, Shortcuts, Mail, Reminders and iMessages eventually do sync and catch up. But when they randomly don’t and you’re counting on them it’s like receiving a hastily scribbled note in your Christmas stocking telling you the gift you were expecting will be arriving later. Certainly survivable, but disappointing and certainly not magical.
While, at times, the reoccurrence of these issues seems random, there seems to be some predictability about it. They far too often (not always) crop up just before or just after an update is released whether it be the next official OS release or the beta for the next version. My hunch, after months of observation, and talking with other users and your elves, is that each time you issue a software update for devices (beta or official), whatever accompanies that on the back end keeps stacking problems on top of unsolved problems.
To be quite honest it feels more and more like regardless of if we run OS betas or not, (I do not), non-beta users are subject to the same vagaries that any beta can bring and/or fall prey to back end operations that are required by these updates.
Mac Notifications in General
Please, oh, please. We all know notifications are tricky. We all know they are a mess. But please, oh, please give Mac users a way to bail out and dismiss all notifications with one button the way we can on iOS devices. Or at least time them out.
Reminder Notifications
I’m very pleased with the continual progress in the Reminders app. I like using Reminders for shared lists with my wife. But the notifications when adding a shared Reminder to a list need to at least follow the same rule as other Reminder notifications do and disappear after a short time, waiting to be recalled. I used to find it humorous that my wife could add a Reminder to our shared grocery list while I was on the way to the store. But not so funny after I picked up the item and cleared the item in the Reminders app, had returned home and placed the item in the fridge only to find the shared Reminder still showed up on my devices. I let some of these linger for a day once. And they never disappeared until I manually removed the notification.

Stand By
This is a nice new feature that I like quite a bit. Please fix it so the widgets I choose to show stay on the screen and don’t change randomly after I’ve set up my preferences. This feature either needs to be less smart or much more intelligent.
Apple Mail
I use Flags and Rules in Apple mail to help me manage my Mail workflow between projects. Different projects have different colored Flags. That works well most of the time switching between Macs. But not always. In fact currently the counts are so drastically off between my two Macs that it’s a little ridiculous. And it’s always changing.

I watch over a course of days how those numbers can change trying to sync up. When the counts get off so drastically, it tells me something is happening server side on the back end. That doesn’t help when I am attempting to use this organization structure to accomplish a task. By the way the differences in numbers is more often than not off between Mac and OS devices also.
I’d also like to be able to more easily track via color distinction those same Flags in iOS by having another menu drop down allowing access to the different color categories instead of just a list of emails with all of the different colored Flags.
When I’m triaging email I’d like to be able to choose a colored Flag after using the swipe gesture to Flag an email instead of having to go back and choose the correct color later.
Consistency Across Platforms
I know things are different between macOS and iOS. And yet, it seems like you keep trying to bring them into more and more into sync. (“Sync” might be a poor word choice there, given all the syncing issues you have. Or maybe it’s just too darn appropriate.) In trying to sync some things up you’ve created some cognitive dissonance and user frustration. These issues cut across Apps and Services like Shortcuts, the Share Sheet, Mail, Notes, Reminders, even Apple Music, Apple TV+ and Apple News. Features are almost the same, but not quite the same enough.
There are times when using a feature on one platform is just a small enough degree different than on the other that it creates a logjam in getting things done and makes me think I’ve lost track of how to perform the task. At times it makes me wish things were more separate and not less. But I know that’s not the goal much less the desire.
Wrapping Up
So that’s it. With the exception of the issues related to iCloud, I think it’s a manageable list. Here’s hoping Apple’s vision for the future includes cleaning up these longstanding nagging issues before adding new ones on top of the old.
Merry Christmas!