By Dan Moren

June 14, 2016 3:31 PM PT

WWDC 2016: Apple’s OS improvements, in the order I want to download them

Note: This story has not been updated for several years.

I’m still processing the massive amount of information that Apple dropped at Monday’s keynote, including poring over all the previews of the upcoming OSes on the company’s website. But sometimes it’s about going with your gut, and my gut is telling me that I’d like to install these new upgrades as soon as humanly possible.¹

I’ve checked in with my gut about which particular upgrades it’s the most interested in, and it very nicely came back with this ordered list, starting with a modest thumbs up, all the way to frothing-at-the-mouth excited.

tvOS

I’m a daily Apple TV user, so it was great to see Apple take some steps towards correcting the biggest issues with the set-top box’s user experience. And just to be perfectly clear, we’re talking Single Sign-On here. Having recently given my parents my old second-generation Apple TV, I can attest firsthand to just how difficult it is for a non-technical person to go through the process of authenticating their apps.

Excited as I am for that streamlining, my enthusiasm is somewhat tempered by the fact that it’s a benefit that just doesn’t come into play that much. Easier setup is great, but I only set up an Apple TV once occasionally. The other improvements: Siri expansion, HomeKit integration, Apple Music, and even the new Apple Remote app are nifty, but none of it is going to immensely change the way I deal with my Apple TV. Dark mode is cool, though. (It would be great if it could auto-switch from light to dark depending on the time of day, Night Shift style.)

macOS

Let’s get one thing straight: Siri on the Mac? It’s about time. But despite that being the most prominent feature of the release, there are still a lot of questions to be addressed about the implementation. For example, one friend commented to me just after the keynote: “I have a Mac mini, which doesn’t have a microphone…how’s that going to work?” Presumably with an external mic, but Apple doesn’t sell its own, so that means picking up a USB mic or, say, a webcam.

The demo was also light on details about what Siri can do: yes, it can search your hard drive, or give you the weather, but what about automation? There’s more to the Mac experience than just finding files. Integration with OS X’s existing voice control would open up a lot of potential power, but do the systems co-exist? Does Siri absorb Dictation Commands? It’s unclear.

To me, the most interesting features that Apple showed off are those related to Continuity: Apple Pay and Auto Unlock, using authentication from the iPhone or Apple Watch in the first case, and Apple Watch for the latter. This is the kind of power I’ve been talking about in terms of Apple leveraging its broad ecosystems of devices: when you already have an authenticated device on your person, does it really make sense to have people enter a password again? Not so much.

Same with Apple Pay: yes, you could wait for Apple to build Touch ID into all of its Macs, but why bother when so many people have an iPhone with Touch ID sitting right next to them? (In cases where you don’t have an iPhone or Apple Watch, or have an earlier iPhone without Touch ID, I wonder what happens: perhaps you just get a text or enter a password?)

On the cloud storage front, Apple’s making a hard play against Dropbox by syncing your Documents and Desktop folders to all your Macs (and making them available on iOS via iCloud Drive). This is the kind of thing Apple should have been doing a long time ago, and frankly, having gotten used to Dropbox, I’m not sure that I’m in a hurry to have all the files on my Desktop (which I use as just a temporary holding place) on all my devices. And then there’s the sticky issue of iCloud reliability, which doesn’t always have the best reputation.

Which is a serious thorn for Apple’s other new cloud-based file feature, Optimized Storage. On the face of it, anything that clears “old” files to give me more disk space gives me the heebie jeebies. Remember the uproar earlier this year when Apple was even suspected of deleting someone’s Apple Music files? Yeah, now multiply that by a thousand for when somebody loses a crucial document.

This isn’t to say that it can’t work, just that I—and many others—are pretty wary about it.² The track record here isn’t the best, whereas many of Apple’s competitors—including Dropbox—have made their names on making data reliability a priority. Also, what happens when you’re offline, or have a bad network connection and need an “old” file? Are you just out of luck? Like Siri, there are a bunch more questions to be answered here, especially before people want to commit their sensitive files to it.

iOS

Let me explain—no, there is too much. Let me sum up. iOS 10 is chock-a-block with things that I’m excited about. I have to be honest: when I added lock and home screen improvements to our iOS 10 wishlist last week, I figured that I was tilting at windmills. And yet, that’s exactly what we got. The Today view has moved from Notification Center to a screen accessible via swiping right from the lock screen, and has widgets that provide quick, glanceable information. Notifications on the main screen are actionable via 3D Touch (and presumably long presses on non-3D Touch devices?).

There are a couple of little touches I appreciated: that notifications no longer cause your wallpaper to darken and blur, for example. That’s contradictory to the idea of picking a beautiful wallpaper image, which was something Apple always promoted. The idea of Raise to Wake, which avoids the “too good” issue where 6s users’ faster Touch ID would skip right over the lock screen.

All in all, iOS is poised to get both a major increase in functionality by opening up many of its apps and services to third-party developers—Maps, Messages, and Siri—and a slight facelift in terms of design, right about the time that the iOS 7 look was getting a bit long in the tooth.

Then there’s the craziness that is Messages. I could have seen Apple’s approach going one of two different ways: trying too hard to be cute and hip, or succeeding by being thoughtful and fun. Much as my curmudgeonly nature wanted me to cultivate an instinctive dislike of the manifold effects and gimmickry in iOS 10’s Messages, I have to say it looks like it just might work. I was more charmed than annoyed—we’ll see if that lasts until after the fifth confetti explosion.

watchOS

I surprised myself a little bit when I realized that watchOS 3 was the software that I wanted to install the most. There are a couple reasons for this, the most obvious being the sheer promise of the improvements in the newest version of the software. But also, it’s a tacit acknowledgment that, unlike my Mac and my iPhone (and even my iPad), the Apple Watch is simply not an indispensable part of my life. If my iPhone or MacBook dies, well, I’m in a tough spot. But I lived a long while without a smartwatch, and having beta software brick it sure wouldn’t kill me.

None of that should undercut the importance of what Apple showed off with watchOS 3. Not just in terms of features, but also in realizing where the missteps in the previous versions were and, as Jason already commented, being willing to simply toss out features that didn’t work.

The Friends button will not be missed by any of my actual friends, whom I have managed to stay in touch with despite not sending them heartbeats and little sketches. Nor will I be pouring one out for the departed Glances, whose reach always seemed to exceed its grasp.

It remains to be seen if the speed and responsiveness that Apple showed off during the keynote will be replicated in the real world, but if it’s even a fraction thereof, it will still be a massive improvement. I also applaud Apple using this opportunity to redirect developers towards making apps that are easy to access and don’t hide functionality away beneath several button presses.

As a brand new type of device, the Apple Watch was a bit like the protagonist of a bildungsroman, unsure of its potential in life, but in watchOS 3, it seems like it might finally have grown into its role.

My frustrations with the Watch have been well documented, and though I rarely go a day without wearing it, I’ve often struggled to find a use for it beyond checking notifications and setting timers for steeping a cup of tea. But the Apple Watch I’m seeing previewed in watchOS 3 looks a lot more like the device we were first sold.

[Dan Moren is the East Coast Bureau Chief of Six Colors. You can find him on Mastodon at @dmoren@zeppelin.flights or reach him by email at dan@sixcolors.com. His latest novel, the supernatural detective story All Souls Lost, is now available for pre-order.]

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