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by Jason Snell & Dan Moren

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By Jason Snell

Hands on with macOS Sierra

The X is dead—long live macOS. With this fall’s release of macOS Sierra, Apple is bringing some familiar iOS features to the Mac, along with interesting interactions with iOS hardware, a dramatic expansion of iCloud, a major update to Photos, and a lot more. I’ve spent the past few days using an early beta, and here are some first thoughts about where Apple is taking the Mac in 2016.

iCloud and on-demand storage

Apple has spent recent years investing a lot of energy into iCloud in general and iCloud’s file storage features in particular. Last year’s introduction of iCloud Photo Library offered users the option of storing their entire photo libraries locally or allowing iCloud to “optimize” storage, storing everything in the cloud and deleting local data as needed in order to free up disk space.

In Sierra, iCloud Drive is expanding in several different dimensions. First, the operating system can optionally sync not just your iCloud Drive folder itself, but your Documents Folder and Desktop as well. Apple reasons that these two folders are where the bulk of a user’s documents reside, and that syncing those files with iCloud Drive (thereby making them available on all your other devices) is a good idea. It also means that if you have two Macs—say, a desktop and a laptop—this feature allows you to keep them in sync (or at least, the Desktop and Documents folders) at all times. That’s great.

So many ways to save.

This is a feature that probably doesn’t scale well, however. I definitely fit the profile of a Desktop file-storer, so Apple’s got my number there, but a lot of the items I store on my Desktop are extremely large media files that I’d never want to sync via iCloud—and would swamp my Internet connection if I tried. Unsurprisingly, Apple has kept the settings on this feature very simple, so my choices are to turn it off entirely or to change my own behavior to work around Apple’s desire to sync my Desktop folder.

Apple’s also offering a feature that lets your Mac arbitrarily delete any of the items in your Desktop and Documents folders that have been stored in iCloud. This is pretty much how iCloud Photo Library works, and I’ve seen it work well there for a year now.

Still, the prospect of my computer silently deleting my files fills me with dread. It’s probably not fair that I feel this way, but there it is: Do I trust iCloud enough to give my Mac free rein to delete my local files? And what happens when I’m on an airplane without Internet when I discover that an image I wanted to use in a presentation was deleted from my hard drive and is therefore inaccessible? I have a lot of questions, and not a lot of answers.

At least in this early version of Sierra, many of macOS’s space-saving features are accessed from a peculiar place: the System Information app, most commonly accessed by choosing About this Mac from the Apple menu, clicking on Storage, and then clicking on the new Manage Storage button. This is where you can turn on the Store in iCloud feature, but that’s not the only way Apple is trying to save space on your hard drive.

The new Storage Management window also offers a few other features designed to ensure free space on your drive. The Optimize Storage command lets you instruct iTunes to remove already-watched movies and TV shows and lets you tell Mail to download no file attachments, or only recent ones. There’s an Erase Trash Automatically feature that instructs the system to wipe any item that’s been in the trash for more than 30 days.

Finally, there’s a Reduce Clutter command that acts like a spring-cleaning utility: Sierra will display your larger documents in various categories (iOS device backups, GarageBand instruments, installed apps, Mail attachments, installation disk image downloads) and let you quickly mark them for deletion or, in some cases, alter system settings to reduce the amount of size they’re taking up. Sierra also works in the background to be better at tidying up things like log files, in order to save space.

In an age where huge spinning hard drives are rapidly being replaced by small-capacity flash drives, I can see the value of allowing the system to store files in the cloud and remove them locally to free up space, and of reducing the amount of space being used unnecessarily.

Still, it’s also hard not to think of the fact that Apple is building out its services business, and by tightly integrating iCloud storage and increasing the amount of data that you can sync with iCloud, macOS Sierra is also an invitation for users to spend more money on iCloud space1.

A Mac take on Siri


It took five years, but Siri has finally made the leap from iOS to the Mac with Sierra. It’s largely the Siri you know, but since a Mac is not an iPhone or iPad, there are a few interesting variations.

First off, you can’t trigger Siri on the Mac with a “Hey Siri.”2 Unlike iOS devices, on the Mac you need to type a keystroke or click on the Siri icon in the menu bar or the Dock in order to begin speaking. Activating Siri brings up a floating window with an audio waveform, and then displays the results of your query in that same window. (You can choose what microphone Siri uses, and whether Siri speaks its results aloud, in the new Siri pane in the System Preferences app.)

When Siri returns answers to your requests in that floating window, that’s not the end of the story. You can drag and drop, or copy and paste, results into other apps, Many results also come with a plus icon in the top right corner, allowing you to pin them to the top of the Today view inside Notification Center. (You can remove them later by clicking an X icon in the same location.)

in El Capitan, Apple added the ability for more natural-language search queries inside Spotlight, and that feature has been rolled into Siri with Sierra. You can ask Siri to display presentations from the last month, and it will oblige—listing up to 10 search results in the floating Siri window, along with a button that will open the complete set of results in the Finder.

If you’re playing music or a video, the system will temporarily mute that audio when you activate Siri, then restore it when your voice query is complete.

In general, Siri on the Mac is pretty much what you’d expect from Siri on other platforms: If you know the right things to say, it will tell you (or show you) what you want to know. If you say the wrong thing, you will very quickly discover the edges of its abilities. I like the ability to add information snippets to the Today view via Siri, and to drag and drop items out of the Siri window into other locations.

What’s surprising about the addition of Siri is how little it has affected other speech-related facets of macOS. Speech-to-text dictation is still a feature, but it’s not connected to Siri in any way—it’s been relocated to the Keyboard preference pane, in fact. The Advanced Dictation technology that allows users to automate complex tasks on the Mac by tying into the system’s scripting interface is also separate.

Photos revamp

A segment of one Memories item.

Apple is adding an entirely new image-recognition engine to the Photos app in both iOS 10 and macOS Sierra. The old Faces interface (which dates back many years) has been replaced with a new engine that analyzes every photo on your device not just for faces but other scenes and objects, like mountains and horses and rainbows and butterflies, but probably not unicorns.

Currently all the analysis remains on the device itself, rather than syncing the results with your other devices via iCloud3. That seems awfully inefficient (and might possibly lead to inconsistent behavior between devices), but it’s better than the old approach, which was that you could assign and define Faces on the Mac, but couldn’t do anything at all on iOS.

The replacement for Faces is a new album called People. While Photos will attempt to match people to names based on their profile photo in your Contacts list, of course you can also assign faces manually. In the early version of Photos I tested, the app seemed to be identifying far fewer faces than the previous version, but it is an early version. The other analyzed elements simply appear as categories you can select when you’re typing in the app’s search field. (You can only pick one at a time, which is too bad—it would be nice to be able to limit to photos of dogs from 2015, for example.)

A list of People.

Another major addition to the Photos interface is the Places view, which puts all of your images onto a map. In previous versions of Photos, you could view small collections of images on a map, but not your entire library.

The new Places view.

And then there’s the Memories tab, a new area where Photos tries to surface interesting stuff from both the recent past and the deep archives. When I checked this tab yesterday, I got images from a trip to the beach that my kids and I took four years ago, some images of an end-of-year school music performance from three years ago, a “best of the last 3 months” album, and a collection of shots from this time last year. Clicking on any memory collection brings up an animated title segment, a collection of images, a map of image locations, and links to related subjects—so theoretically you can just keep clicking through and seeing more collections.

There don’t seem to be major changes in the fundamentals of Photos, though Apple says that the algorithm that drives the auto-enhance button has been updated to produce more striking images.

Enhancements old and new, with the original at the center.


One of the banner features introduced in Yosemite was Continuity, a feature that let Apple devices in proximity to one another—whether they were Macs, iPhones, or iPads—share some information with one another. Up to now, these features have been largely about passing small amounts of information—like the web page or email message being viewed—between devices. Sierra goes beyond that to enable the security features of other Apple devices to extend the security (and convenience) of the Mac.

Auto Unlock uses an Apple Watch to unlock a Mac as long as it’s within three feet of it. For the feature to work, the Apple Watch must be unlocked—meaning you’ve entered in the passcode or unlocked your phone, and it’s been continuously attached to your wrist since then. When a Mac is unlocked with this feature, the unlocking Apple Watch will vibrate and display an alert, so you shouldn’t be able to unlock a Mac accidentally. The range is specifically limited to prevent inadvertent Mac unlocks from farther away.

Apple has added Apple Pay to Safari for the Mac, allowing Mac users to pay for stuff on the Web more conveniently than ever before. Apple says it’s working with web sites and popular payment systems to make Apple Pay available in many places on the Web this fall.

Apple Pay support relies on a nearby Apple Pay-capable iOS device for authentication. An Apple Watch will do the trick, or an iPhone. (iPads won’t work.) Once you authorize payment (with a Touch ID press on the iPhone or a double-tap on the main button on the Apple Watch), Safari will allow you to purchase the item in question via the Apple Pay system, just as you can today on iOS devices.

It would be awfully nice if you could make purchases without additional hardware, but so far no Macs have been built with the secure infrastructure that Apple has built into iOS devices and the Apple Watch.

(One nifty feature: Apple says that web developers can actually code sites so that the Apple Pay button only displays when an eligible device is in proximity of the Mac.)

A more traditional-feeling Continuity feature is the addition of a shared clipboard in iOS 10 and macOS Sierra. This clipboard feature has been created with care; it only works when your devices are within Continuity range, the data on a clipboard is only transferred when you decide to paste, and if there’s no action taken on a shared clipboard in two minutes, the sharing expires. The goal, according to Apple, is to enable very simple data transfer between devices—copy it here, paste it there—without complications like accidentally stomping on your Mac’s clipboard while you’re somewhere else.

And the rest…

There are always a zillion of other small features in macOS updates. Of course, Sierra’s no different. Between now and the final release, I expect we’ll discover many fun surprises along the way. But here are a few of the smaller, additional features that this new version will bring:

Tabs aplenty. Do you like tabs? If so, you’ll be happy to know that Apple is making it as easy for most apps to create a single window with multiple tabs as it is to create multiple windows. There’s a new setting in the Dock preferences pane that’s called “Prefer tabs when opening documents,” that gives you three options: in full screen only, always, and manually. When always is selected, most (but not all) apps will open documents by adding a new tab for that document to the existing window.

The behavior is pretty much identical to what you’ll find in Safari. You can use the command-bracket keyboard shortcut to move through tabs, drag to rearrange tabs, and even drag a tab out to bring it into its own window.

Picture in Picture. This iOS 9 iPad feature makes its way to the Mac with Sierra, and I like it a lot. I often find myself wanting to keep video running on my Mac somewhere, but doing it can be a challenge. I end up resizing the browser window to hide most (but never all) of the wasted space, and then I try to park it somewhere where the video won’t be inadvertently covered up by other windows.

Picture in Picture in action with a Vimeo video.

Picture in Picture solves all of this. For compatible video—standard HTML 5 video out of the box, but other web video services can hook into picture-in-picture with some basic modifications—you can click the Picture in Picture icon and the video flies out of its web pages and into a floating box containing just the video (and some playback controls, when you move your cursor over it). You can resize that box and drag it to any corner of screen, just as you can on the iPad. Or hold down the Command key and park it anywhere on your screen.

I love it already and wish it were supported by all of my favorite video services, but I’m sure it’ll get there. The only complaint I’ve got is that it’s so easy to click the Picture in Picture button in a web video and then close the Safari window that spawned it. That doesn’t work — if you close the webpage that originated the video, the video dies too. I’m not quite sure what Apple should do here—maybe minimize that window/tab and stick it in the Dock or something? But it’s a minor quibble.

Messages. Messages is a major focus of iOS 10. macOS Sierra, not so much. Apple is making an effort to make Messages on the Mac capable of receiving a lot of the fun stuff created by users of iOS 10. Mac users will be able to see stuff like animations and invisible ink, but won’t be able to create any of them. Mac users will be able to generate “tapback” reactions to messages, and will see rich web links (with page titles and images) rather than bare URLs when they send those, or are sent them. But for most of the fancy new Messages features, macOS Sierra is about playback, not creation.

Sharing in Notes.

Notes. The big news is that the Notes app on the Mac has finally hit the big time: It’s got a preferences window. More practically, Notes for Mac on macOS Sierra will have the same new iCloud sharing features that will be available on iOS 10. Click on the sharing icon in any iCloud-based note, and you can add collaborators via Mail, Messages, Twitter, Facebook, AirDrop, LinkedIn, or the old-fashioned “a link you put on the clipboard and send to someone yourself.”

Opening apps. Apple has eliminated the security setting that prevented the system from complaining when you launched an app that was neither downloaded from the App Store nor signed by a verified developer. You can still launch these apps, but the first time, you’ll need to right-click on them and choose Open from the contextual menu, then approve the launch of the dirty, dangerous app in the following dialog box.

Hike into the high Sierra

The features of Sierra I’m most excited about have to do with its interoperability with the Apple Watch and iPhone, which I haven’t been able to test directly yet. The opportunity to sync more stuff to iCloud Drive is welcome, though I’m not sure I’m willing to change my habits just to gain syncing of my Desktop folder—and I’m also not sure I’m ready to let Apple delete my files automatically and rely on cloud backups.

As for Siri, I’m glad to see its arrival on the Mac at long last. The implementation is more than I’d feared, but less than I’d hoped. The access to the same data services as on iOS is great; I hope the development of more Mac-specific features continues, including better integration with the powerful automation features already built into advanced dictation. (And yeah, I kind of wish it could optionally be activated by a trigger word, as it is on iOS.)

In any event, Sierra is shaping up to be a solid release—with or without the X. I’m looking forward to spending time with it over the summer to see how it progresses on its path to its arrival in the fall.

  1. If only families could share iCloud space… ↩

  2. Apple’s take is that Mac use tends to be active in a way that iOS use isn’t, and so triggering Siri with a keystroke or click makes sense. ↩

  3. Apple’s Craig Federighi said last week that Apple could add that feature in the future, so here’s hoping. ↩

See more macOS Sierra coverage.

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