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Six Colors coverage of macOS Sierra

By Jason Snell

Syncing feeling: iCloud Drive in macOS Sierra

Documents and Desktop, nestled into iCloud.

So many of macOS Sierra’s new features are about freeing up space from our fast-but-tiny solid-state drives. In addition, Apple has extended support for iCloud Drive to optionally include your Desktop and Documents folder, and mixed those two approaches together to create a third feature, called Optimize Mac Storage.

I like what Apple’s going for, but both of these features have problems, and some of them bit me when I was writing my review of Sierra. Let’s take a much closer look at what’s going on with syncing and optimizing, including the bugs, the missed opportunities, and the workarounds.

Syncing Documents and Desktop to iCloud Drive

In Sierra, iCloud Drive finally gets to break out of its own protected folder and into the system at large.

In reality, that’s not quite what’s going on—when you first install Sierra, you’re asked if you want to sync your Desktop and Documents folders with iCloud. If you turn this feature on, your Desktop and Documents folders are really moved inside iCloud Drive, with the old locations linked to your home folder so that everything behaves more or less normally. (Except when there are bugs—a few of my apps seemed to get confused when those folders changed locations.)

iCloud syncing is pretty robust, and once I got up and running with this feature, it worked as advertised. However, the act of turning it on can be terrifying, especially if you’ve already turned it on while using a different Mac. If your Mac discovers that another Mac is already syncing its Desktop to your iCloud Drive, Sierra will create new folder called “Desktop - Your System Name” inside the Desktop folder within iCloud, and move your files inside. (The same thing happens with your Documents folder.)

What this looks like in the Finder: All your files disappear off of your desktop. Maybe a few new files from your other Mac appear. If you keep your key files on your Desktop, it can be terrifying. However, if you look around, you’ll probably see that “Desktop - Your System Name” folder, and all your files should be in there.

Apparently Apple didn’t anticipate this moment of terror, though it should’ve seen it coming. The right thing to do is probably to generate a warning for users, and maybe leave that folder open in a Finder window. Even better would be to give the user a few options when they turn on Desktop and Documents syncing on a different Mac—keep the two Desktops separate, merge them together, or set either one of the Macs as the “real desktop.” But right now, the first Mac wins and the next Mac stuffs its files into a subfolder and waits for the user to sort it out.

Because I wrote a book about Photos, I bought a huge amount of iCloud space to sync my entire Photos library. As a result, I was able to sync everything in my Desktop folder—even huge audio files—to iCloud without difficulty. If you don’t have enough free iCloud space to sync your Desktop and Documents folders, Apple will offer you the exciting opportunity to buy more. If you decline, Apple won’t let you enable this feature.

(Later, if your folders surpass the amount of space available on iCloud, you’ll get an alert and your files will stop syncing with iCloud. They’ll still be present on your Mac, safe and sound, but syncing will stop until you free up or purchase more iCloud space.)

The trouble with optimizing iCloud storage

Combine the concept of purgeable space and the ability to sync more files with iCloud and you get a third key feature of macOS Sierra. When you turn on syncing of the Desktop and Document folders, the Optimize Mac Storage feature is turned on. (You can turn it off in the iCloud Drive section of the iCloud Preference Pane, and probably should, for now.)

Optimize Mac Storage is a feature that defines files that have been uploaded to iCloud as purgeable, more or less. Apple prioritizes your files so that things you’ve accessed recently will be kept around, but items you haven’t accessed for a long time can be removed. When a file is removed, it’s gone from your hard drive, but it lives on in the cloud, and can be downloaded again by clicking an icon in the Finder or when it’s demanded by an application.

Scary, right? But again, if everything’s working perfectly, you’ve just granted that tiny SSD on your MacBook an extra few hundreds of gigabytes of storage, because it can offload your old junk to the cloud. And if it turns out you need it, you can get it back.

If everything’s working perfectly. And if the system can truly differentiate between files you need and files you don’t.

So something bad happened when I was working on my review of macOS Sierra. As a responsible reviewer, I need to use all the features of a new operating system. That comes with some risks, but that’s why I’m here. Risk (of losing data) is our business.

Here’s what happened: While I was working on a podcast-editing project in Logic Pro X, a bunch of my audio files were removed by Optimize Mac Storage. I keep all my key files and projects on the Desktop, as many people do, and since this is a feature that’s designed to keep your work in sync, I decided I was not going change my workflow one bit.

Apple has since told me that I absolutely ran into several different bugs, as well as a few quirks of the file-management process. Many apps store all of their asset files in a single package file—it’s really a folder, but all the important files are stuffed inside so that if you move the package, everything comes along for the ride. A Keynote presentation file is actually a package with a Keynote document and all of the images and movies you dragged in, all bundled together.

Optimize Mac Storage works great with packages. It’s not going to delve down inside a package and get rid of your files—old projects can be optimized away, but new products will remain on your drive, and nothing gets plucked out of the inside of projects.

The problem with some apps—and Apple’s Logic Pro X and Final Cut Pro X fit into this category—is that either they don’t use packages, or stuffing all your files inside a package is optional. My podcast template keeps audio files in the same folder as my Logic project files, but they don’t live inside a package.

Now, it turns out that App developers can take advantage of file-coordination APIs to designate all the files that a given project is using, even if they’re not inside a package. If Logic Pro X used those APIs, perhaps my files wouldn’t have been touched, because iCloud would recognize that they were part of an active project. Alas, not even Apple’s own apps support all of Apple’s APIs. (Optimize Mac Storage apparently looks at the last time you opened a file in the Finder as a way to help determine the age of a file, but if you open a project file and that file then reads from other files, the feature doesn’t consider them actively used.)

The setup of my project folders, Logic’s lack of support for file coordination, and the bugs that made my Mac think it was much more space constrained than it actually was—this was the situation that conspired to make Optimize Mac Storage look at a few 14-day-old 600MB audio files and decide that they were old junk.

Pro tip: Turn it off or move key files elsewhere

With any luck, Apple’s hot on the case of fixing the bugs. Perhaps the teams in charge of Apple’s pro apps are working on coordinating project files a bit more aggressively. And I suspect that I might be a little responsible for this new Apple tech note, which suggests that if you’re using a pro app, you should move your projects out of synced folders or turn off Optimize Mac Storage.

Yep, that’s Apple saying that people who use pro apps should just turn off or avoid using a major new feature of macOS Sierra. It burns a little—what’s the point of making new productivity features if some classes of Mac user just shouldn’t use them? What’s worse, it points out the larger risk in turning on Optimize Mac Storage: If you keep key files outside of a package—images you’re planning on dropping into a Keynote presentation, for example, but haven’t yet—you risk them being deleted by Optimize Mac Storage.

If your internet connection is permanent, fast and unmetered, this is no big deal. If you’re working on an airplane and discover that one of your files you were counting on is gone, welp… that sucks for you. Optimize Mac Storage offers no user interface, so there’s no way to designate certain files or folders as un-purgeable. It’s all or nothing. Either you take your chances or you walk away.

For many classes of Mac user, the risks are low and the benefits are great. For other classes, the right answer is to do what Apple recommends in its tech note: walk away.

See more macOS Sierra coverage.

By Jason Snell

When free space isn’t free: Purgeable storage in macOS Sierra

For years, the storage inside our computers just kept increasing. But with the advent of solid-state drives, which are less prone to failure, dramatically faster, and more energy efficient than spinning hard drives, there came a tough transition. Instead of having a terabyte or two of disk space, maybe you’ve only got 250 or 500 GB. Maybe you used to never think about running out of space, and now every so often your Mac throws up that terrifying warning box that your disk is almost full.

Apple recognized this, too, and to its credit, it made this transition one of the main features of macOS Sierra. A lot of the stuff on our drives doesn’t need to be there. It either isn’t necessary (log files, used app installers, and the like), or it’s just a duplicate of something that’s stored in the cloud.

The result is a whole raft of features in macOS Sierra that are all about freeing up more space on your drive. One of the biggest changes affects about how free space is calculated and displayed.

Free space and purgeable space


macOS displays the amount of free space on your drive in a few places, including:

  • If you’ve got the Status Bar turned on in the Finder (View: Show Status Bar or Command-slash), you’ll see it at the bottom of the window

  • If you’ve got Finder preferences set to show hard disks on the Desktop, you can turn on Show Item Info from the View Options panel (Command-J)

  • If you select your drive from the Desktop or from the Computer window (Go: Computer or Command-Shift-C) and choose Get Info (Command-I)

  • You can choose About This Mac from the Apple menu and click the Storage tab.

  • In macOS Sierra, you can activate Siri and ask it how much free space you’ve got.

The Storage tab in About this Mac has been redesigned for macOS Sierra to give you more information about what’s filling your drive. The mysterious “Other” area of the storage graph is gone, and there’s much more granularity about what’s using that space, including unexpected space hogs like GarageBand and iTunes backups of iOS devices. The new Manage button, above the right edge of the graph, can help you reduce that stuff.

But if you look at the right end of the graph you’ll find two blocks: Free Space, labeled in white, and Purgeable, labeled in white with a diagonal gray pattern. In macOS Sierra, there are two different kinds of free space: Free and Purgeable.

Free space is what we’ve always known it to be. It’s space on disk where there’s nothing 1, that’s ready to have data poured into it. Purgeable space is different. Purgeable space is a collection of files that are really on disk, ready to be read or modified or added to at any time—stuff like files stored in iCloud, dictionaries you haven’t used recently, certain large fonts (especially of Asian languages) that you may never or rarely use, movies and TV shows you’ve already watched (and are re-downloadable from iTunes), and photos and videos in that are synced with iCloud Photo Library (if the Optimize Mac Storage setting is turned on in Photos preferences).

These are real files, but Apple considers them expendable. They can be deleted immediately, without warning, in order to free up disk space, because they can always be downloaded again later.

Now here’s the big change in macOS Sierra: Apple adds the amount of truly free space to the amount of purgeable space, and that’s what is displayed on your Mac as the amount of free space on disk. As I write this, my boot drive has 51.3GB of free space—and 22.6GB of purgeable space. In the old days, this would be reported to me as 51.3GB free. In macOS Sierra, it’s reported as 73.9GB free.

According to Apple, if I were to try to copy a 60GB file onto my drive, it would just work. The system would work in the background to purge enough stuff to fit my file and keep a decent amount of free space on the drive so that my Mac wouldn’t slow to a crawl, which happens when your disk is nearly completely full.

Now, when I was writing my review of macOS Sierra, I ran into a few bugs on this front. My system became confused about the real amount of free space on my drive, and prevented me from performing an iOS device backup when I had plenty of space. None of my data was lost, but I was prevented from performing actions that shouldn’t have been a problem. At one point—you can see this in the screen shot at the top of my Sierra review—my Mac couldn’t decide how much free space it really had. Siri said 30GB, but the System Information app said 55GB 2.

I’m confident that Apple will squash these bugs in short order. But the new concept of free space is here to stay. In an ideal world, your Mac should treat that free space as real free space, and there’s no need to peek behind the curtain. In the shorter term, there will probably be bugs and incompatibilities, and if you’re someone who cares about what’s going on behind the scenes of your Mac, you should be aware that not all free space is the same.

  1. Okay, pedants, there’s actually data there, but it’s essentially garbage—the system can overwrite it when it wants. ↩

  2. I notice now that it also claims my boot volume was 120GB in size, when it’s actually 466GB. More bugs! ↩

See more macOS Sierra coverage.

Jason Snell for Macworld

7 things to try in the macOS Sierra public beta ↦

A little less than a month after unveiling macOS Sierra and giving developers a sneak peek, on Thursday Apple is opening up macOS Sierra to members of the public via the Apple Beta Software Program. The first public beta is presumably the same version as Developer Beta 2 released Tuesday.

I’ve been using Sierra for a few weeks now; check out my hands-on article as well as eight hidden features that I think you’ll like. If you’re thinking about installing Sierra, here’s what you need to know.

Continue reading on Macworld ↦

Linked by Jason Snell

Hands on with macOS Sierra

Excited about the public beta of macOS Sierra? Don’t forget to read my lengthy hands-on preview, which I wrote late last month based on the first developer beta. It’s all still in there!

By Jason Snell

Where should I install my iOS and macOS betas? A guide.

macOS sierra is coming Thursday. Here’s where you should install it:

  • Nowhere, if you aren’t willing to constantly back up all your data and take the risks of having an unstable Mac in your life for a few months
  • Nowhere, if you aren’t willing to use the Feedback Assistant app to report to Apple about the bugs you’re finding
  • On a secondary Mac, i.e., not the one you use to do your job every day, or
  • On a separate partition on your Mac, so you can re-boot into El Capitan for safety, or
  • On an external drive attached to your Mac—I bought an external SSD so I could run macOS Sierra on my iMac without messing with my existing internal drive set-up.

iOS 10 beta is also due today. Here’s where you should install it:

  • Not on your main iPhone
  • Not on your main iPad
  • On an iOS device that you don’t rely on

The Mac has it easy—you can always reboot from a different drive if the beta software is giving you trouble. On iOS, once a device is on a beta it’s hard to revert. You’re on it for the duration. This is why you should avoid using iOS betas on your main devices until very late in the game, if ever.

See more iOS 10 coverage.

See more macOS Sierra coverage.

By Jason Snell

macOS Sierra public beta arrives today

The first macOS Sierra public beta is rolling out later today, according to Apple. Presumably based on the same or similar code to the second developer beta of macOS Sierra, this one’s available to everyone who’s in Apple’s Beta Software Program. Once you’re in the program and on the public-beta train, new public-beta updates will appear in the normal Software Update system throughout the summer, and you’ll be upgraded to the final version in the fall.

For a whole lot more about macOS Sierra, check out my hands-on article from last month.

Among the changes in this public beta are a bunch of bug fixes and a new keyboard shortcut for Siri: holding down the command key and the spacebar until Siri activates.

This will be an interesting public beta cycle for Apple; though the company doesn’t use its customers’ photos as the basis for the machine learning photo engine inside Photos, the public beta should be one of the first major tests of the engine. I’m curious if Apple will solicit users’ photos as a way to test its functionality, and gauge user feedback about how well it’s working so far.

And this is a key point of being on the public-beta train: using the Feedback Assistant app to tell Apple about bad stuff you see, and things you don’t like. Just as developers know to use Apple’s web-based bug reporter, users of the public beta should use Feedback Assistant to let Apple know if things just aren’t working right.

After all, this is a beta. Things will change and improve over the summer. And if you’re up for the challenge you can help.

Before you run to install the beta, some final words of advice: Back up all your data. Don’t install this on your main Mac’s main hard drive—either use a secondary computer or a separate partition or an external drive. And never work with data that you aren’t also backing up somewhere else, especially if you’re testing out the new iCloud and space-saving features.

See more macOS Sierra coverage.

Linked by Dan Moren

New macOS Sierra security feature may harm more than help

Rogue Amoeba’s Jeff Johnson takes on a new security feature of Sierra, Gatekeeper Path Randomization:

We support Apple’s efforts to increase security for all users on MacOS. However, this specific change will have a great deal of negative impact, while providing no security gain for the vast majority of apps. Users will be stuck with apps that don’t work (or update) as expected. The simple change we’ve proposed would still provide Apple with the desired security benefits, while removing the downside this will cause for users. We hope you’ll duplicate our radar, and encourage you to test your software on 10.12 for possible problems.

I’d heard about this during WWDC, but Jeff does a nice job of laying out why sometimes security measures cause more problems than they actually end up solving.

Jason Snell for Macworld

8 hidden features of macOS Sierra ↦

It’s been a week since macOS Sierra was announced by Apple, and I’ve gotten a chance to spend a few days using it. If you’ve only seen the highlights from Apple’s keynote, though, you may have missed a bunch of cool features that have flown beneath the radar. Here’s a look at some interesting features that you might have missed.

Continue reading on Macworld ↦

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.

Continue Reading "Hands on with macOS Sierra"

See more macOS Sierra coverage.

Dan Moren for Macworld

With Sierra, Apple lets the Mac be the Mac ↦

While big updates like iOS 10 and massive rethinks like watchOS 3 might have commanded the lion’s share of attention during Apple’s WWDC keynote and the ensuing aftermath of discussion and Zapruder-level dissection, it’s worthwhile to pause for a moment and consider the state of Apple’s most venerable platform, the Mac.

No longer burdened by its increasingly dated X-laden moniker, the rebranded macOS got a major addition in the form of Siri, as well as some more minor improvements sprinkled throughout the OS.

But to me, the big message to take away from Monday’s presentation is that Apple is all too happy for the Mac to share features and technologies where it makes sense, but to still let it stand on its own two legs and be the best version of itself.

Continue reading on Macworld ↦

By Jason Snell

WWDC 2016: Four platforms, quick reactions

This is how Apple advances the four operating systems it develops: On a Monday in June at its annual developer conference, it announces the high-level details of the next major update of those operating systems. Developers get access to an early test version of the operating system that day; the general public will get the option to upgrade for free sometime in the fall.

That Monday was today, and we got to see previews of iOS 10, tvOS 10, watchOS 3, and macOS Sierra. Developers will now spend their summer planning new versions of their apps to take advantage of new features of those operating systems. Hardy users will test-drive public releases of the new operating systems starting in July. Thus begins an annual tradition, the summer of new Apple software.

(For some audio reactions to the contents of the keynote, check out Upgrade 93, recorded 90 minutes after the event ended.)

Here’s a quick gloss on the major announcements:

watchOS 3

Apple had the choice between doubling down on some of the bad design decisions of the original Apple Watch OS, or tossing them away and coming up with something new. They did the right thing: merging Glances with apps; retasking the side button with bringing up the new app dock; and allowing key apps to run in the background and launch quickly. One of the most common tasks of the Apple Watch, responding to messages, will become much less complex. You can “scribble” text replies and watch as they’re converted to text, the same idea Google recently introduced for Android Wear. Fitness apps will have more power, including the ability to run in the background and have access to all watch sensors.

This is all good. When the Apple Watch was first announced, Apple was taking a guess about how it would be used. Over the past year, we’ve all learned a lot about how the Apple Watch works in the real world. Apple has been taking notes. I’m encouraged by the signs of change.


The tvOS update seemed to be the most minor of the four Apple platforms, but still: Single sign-on will make it much easier for cable or satellite TV subscribers to take advantage of video streaming apps without having to repeatedly log in with their credentials. More live TV deals make the box more appealing for cord cutters. The Remote app will finally become a full Siri Remote. And those who prefer to watch their TV in the dark will have their retinas saved by a new dark mode.

tvOS is still in need of a lot of refinement. Unlike some of Apple’s other platforms, this feels like one that’s in constant flux, with new features and fixes being pushed out a lot more regularly than once a year. It’s been necessary in order to address some major shortfalls of the product’s initial release last fall; I hope this pace of progress will continue in the future.

macOS Sierra

It finally happened. After a decade and a half, Apple has retired the X—all hail macOS. The California place names, however, remain intact, as this name refers to our very own mountain range, the Sierra Nevada.

As has been the case with most recent macOS updates, Sierra has a lot of features that connect the Mac with other Apple devices. You’ll be able to unlock your Mac with an Apple Watch, and sync your clipboard among all your Apple devices. Apple Pay will be integrated with Safari for easy web purchases. A new picture in picture feature will let you float a video in the corner of the screen, just as you currently can on the iPad.

iCloud Drive is being extended in some interesting ways, including automatic syncing of the Desktop folder, and a systemwide storage optimization feature that does for your files what Photos did for your photo library—offload it into the cloud when you’re running low on drive space.

Some people love windows, and other people love tabs. If you love tabs, macOS Sierra will thrill you, because it will feature a tweak that lets apps spawn new windows as tabs inside an existing window. (I am not really a fan of tabs, so this feature is not for me.)

And then there’s Siri, which comes to the Mac for the first time. The Mac had had voice control features for a while, but now the entirety of the Siri feature set appears to be embedded into the Mac, including some fancy additions like hooks into spotlight for file searches, and the ability to save searches (and potentially other stuff?) in Notification Center.

It all sounds good, but of course, the devil is in the details. This summer’s beta releases will tell the tale.

iOS 10

Every time I say iOS 10 I hear “OS X”, and it’s going to be a while before I get over that. Oh well. As always, the latest iOS revision offers an avalanche of new features, including big changes to the lock screen (including solid 3D Touch additions), Control Center, and Notification Center.

The biggest story for developers is this: iOS 10 is a door that seems to be swinging wide open. Developers can now hook their apps directly into Siri for the first time, though for right now it’s limited to a few types of apps: messaging, ride booking, photo searching, workouts, payments, and VoIP calling. More will undoubtedly follow down the road. There’s also a new Maps integration that lets apps connect directly to the Maps app and perform actions inside, and Messages integration with apps as well. iOS used to famously be walled off—apps were all islands unto themselves, more or less. iOS 10 is set to bust down more of those walls.

Finally, there’s Messages. What was previously an unassuming text-messaging app has gotten a radical makeover. If you think messaging is all about sending texts, you have not been paying attention. Some of the biggest apps in the world are messaging apps, from SnapChat to WeChat. People love sending emojis, stickers, and other fun reactions to each other. And Apple has clearly gotten the religion: the new Messages is full of stickers, emojis, animated reactions, and even whole-screen takeover animations with sound effects. Yes, your friends may annoy you with these features if you’re a stick-in-the-mud. But all told, these features give Apple’s own message service a chance to not be completely irrelevant to a new generation of phone users.

The most disappointing thing about the keynote was something not mentioned very often: the iPad. iOS 9 added numerous solid iPad productivity features, but there were almost none mentioned in the iOS 10 section. I’m hopeful that some new iPad features are bubbling beneath the surface, ready to emerge during the summer betas or even in a 10.1 update later this fall. Don’t let this be all that iPad users get until next year, Apple.

There’s a whole lot more to cover, and a whole week of festivities in San Francisco this week, too. Stay tuned to Six Colors for a whole lot more in the days ahead.

See more iOS 10 coverage.

See more macOS Sierra coverage.