3 unreliable iOS and macOS features that Apple needs to fix

Sometimes, it doesn’t “just work.”

apple reminders mac icon
Apple

Virtues are so often a two-edged sword: your best qualities can also be your worst. Apple's certainly no stranger to this; the company prides itself on simplicity and ease of use, but those same qualities can often backfire and yield situations where its products and technology don't work quite right under less than ideal circumstances.

Many of us are used to technology not working right, but that doesn't necessarily make it any less frustrating when our devices behave in seemingly illogical ways. Computers, after all, are incredibly literal devices—on the one hand, they only do what we tell them to do; on the other hand, sometimes they can interpret what we tell them in pretty strange ways.

I've used a lot Apple products over the last 25 years, and while they're more powerful than ever, they can also seem more inscrutable than ever when things go wrong. Just in the last week, I've run into a handful of issues—mostly cloud- and network-based—where the company could do to spend some time improving reliability and living up to that self-imposed mantra: "it just works."

1. Reminders

I use Apple's built-in Reminders app to track most of the things I need to do every day, from my personal and work to-dos to my shopping list. The latter I also share with my girlfriend so that when either of us happens to go to the grocery store we know everything we need to get. But it's been an absolute mess when it comes to syncing those items between our lists—sometimes it seemingly works fine while other times it fails to add items to the other person's list. 

The problem is that with Apple's vaunted approach for simplicity, there's little indication of what to do when such syncing doesn't work. Sometimes you sit and wait and the items pop in eventually. Sometimes force quitting the app will work. Sometimes restarting the phone. Sometimes you even have to turn Reminders off entirely in your iCloud settings and turn them on again. Sometimes none of these things work and you have to nuke it from orbit just to be sure. 

Apple seems to have an allergy when it comes to putting controls related to syncing anywhere in its apps. Not that surfacing such controls is always a fix, but at worst it has a placebo effect that lets us feel as though we have some measure of control over the problem, rather than simply throwing up our hands and cursing. And it's the least the company can do if the feature isn't going to work seamlessly. 

2. iCloud Keychain

iCloud Keychain is one of those technologies that had a rough start, but has proved to be invaluable. You can certainly get more features and control out of a third-party password manager like 1Password, but the deep integration that iCloud Keychain features—especially on the traditionally locked-down iOS—makes it a solid place to start for those looking to up their security. 

When it works. 

Last week, I had to create an account on a website, which I did on my iMac, and then had to subsequently log in on my iPhone. I took advantage of the ability to randomly generate a strong password, figuring it would sync over to my phone. It didn't. Which meant I was left to log in by looking up the password on my Mac and then laboriously typing it in on my phone—the exact thing I'd been hoping to avoid. 

Sync is a hard problem, for sure, but keychain sync is particularly important because something that works unreliably is just as bad—if not worse—than something that doesn't work at all. It encourages people not to trust the technology, which in this case could mean using weaker passwords so that they're easier to remember when entering on other devices. If people are going to truly rely on this feature, then it needs to be bulletproof. 

3. Mac/Apple Watch compatibility 

So far, we've looked at a couple features that are, if not critical, at least result in some pretty significant downsides when they don't work well. Let's move on to something that's just straight up annoying in its inconsistency: unlocking your Mac with your Apple Watch.

This heavily hyped feature first arrived in macOS Sierra and watchOS 3 and its efficacy was...not great. When it worked it was extremely handy, but in my experience—and the experience of many of those I've talked to—it has been incredibly unreliable. Sometimes a Mac seemingly just can't talk to the Apple Watch and you're left at a spinning password prompt until it would have just been faster to enter your password. When you try to troubleshoot such problems, you once again run into situations where the only real option is to try turning things off and then on again. When I've encountered these situations, the feature invariably starts to work again at some point, but I have no idea how I fixed it and what occult steps I might need to take next time it breaks again. 

I've heard various rationales for why this particular feature is so unreliable, but in the end it doesn't really matter. And for something that was touted as a significant benefit, it's disappointing when it only works at a stretch. 

It's all well and good to roll out great new features, but if you're pushing the envelope at the expense of reliability, it can often feel like one step forward for two steps back. Remember, Apple: Nobody's ever been impressed at a feature demo that needs a lame explanation of "Oh, when it works, it's cool."

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