macOS Sierra Review

Over the past several years, Mac OS X macOS releases have gotten smaller and less exciting.

OS X Yosemite brought a new design to the Mac, but past that, most users can’t tell the difference between it and El Capitan, let alone what was new in Mountain Lion or Mavericks.

As I’ve written before, I think the lack of excitement in big macOS releases is mostly okay. The Mac is a stable platform that is still growing, but at a much slower rate than Apple’s front-and-center operating system, iOS.

But it’s September, so there’s a new release to look at: macOS Sierra.

System Requirements & Bundled Applications

The days of unchanged system requirements for new versions of macOS have come to an end. Here’s what can run Sierra:

• MacBook (Late 2009 or newer)
• MacBook Pro (Mid 2010 or newer)
• MacBook Air (Late 2010 or newer)
• Mac mini (Mid 2010 or newer)
• iMac (Late 2009 or newer)
• Mac Pro (Mid 2010 or newer)

Handoff, Instant Hotspot, Mac-to-iOS AirDrop, Apple Pay, Metal and Universal Clipboard are supported by these models:

• MacBook (Early 2015 or newer)
• MacBook Pro (2012 or newer)
• MacBook Air (2012 or newer)
• Mac mini (2012 or newer)
• iMac (2012 or newer)
• Mac Pro (Late 2013)

Auto Unlock with Apple Watch is supported by Mac models introduced starting in January 2013, and requires two-factor authentication on your Apple ID.

The list of bundled applications that come with a clean install remains unchanged:

• Automator
• Calculator
• Calendar
• Chess
• Contacts
• Dashboard
• Dictionary
• DVD Player
• FaceTime
• Font Book
• iBooks
• Image Capture
• iTunes
• Launchpad
• Mac App Store
• Mail
• Maps
• Messages
• Mission Control
• Notes
• Photo Booth
• Photos
• Preview
• QuickTime Player
• Reminders
• Safari
• Siri
• Stickies¹
• System Preferences
• TextEdit
• Time Machine

The Utilities folder is full of familiar icons, as well:

• Activity Monitor
• AirPort Utility
• AppleScript Editor
• Audio MIDI Setup
• Bluetooth File Exchange
• Boot Camp Assistant
• ColorSync Utility
• Console
• Digital Color Meter
• Disk Utility
• Grab
• Grapher
• Keychain Access
• Migration Assistant
• System Information
• Terminal
• VoiceOver Utility

Disk Utility uses the same somewhat confusing user interface Apple introduced last year. Console and System Information have both seen big upgrades this year, but more on that in a bit.

About This Review

For this review, I spent about a month running macOS Sierra on my main system, a Mid 2015 15-inch MacBook Pro with Retina display with a 2.5 GHz Intel Core i7 and 16 GB of RAM.

I have also spent time with Sierra on an Early 2015, 12-inch MacBook with Retina display running on a 1.2 GHz processor and 8 GB of RAM.

My MacBook Pro simply runs circles around the little MacBook, and Sierra didn’t do anything to change that. Both El Capitan and Sierra run perfectly fine on the MacBook, but users of that machine should take some time off work when they decide to update their OS. It takes forever.

What’s In a Name?

As I wrote in June, Apple using “macOS” as a name isn’t completely unprecedented:

Yesterday, OS X got renamed macOS to better match its mobile and TV-bound cousins. While I can get behind everything matching, lots of people have been rolling their eyes a little bit at the lowercase m.

The reason is a pretty good one. Before the days of Aqua and the Dock, the Mac operating system was named “Mac OS.”

While I’d like to see Apple give the Mac a capital M, I am onboard with the change.

As a quick note, let me say that I will still refer to specific versions of the operating system by their proper names, such as “Mac OS X 10.4 Tiger.”

However, I am now using “macOS” to refer to all versions of the non-classic Mac operating system when speaking in generalities. For example:

Previous versions of macOS had way too much brushed metal in their interfaces.

Siri

Five years after it first debuted on the iPhone 4S, Siri has finally come to the Mac. Without a doubt, it’s the single biggest feature in Sierra.

Triggering Siri can be done several ways. Sierra includes Siri in the Dock and menu bar, where the service uses a colorful icon. Holding Option+Space will also invoke Siri. All of this and more can be tweaked in a new System Preference pane:

No matter how you trigger it, any playing audio — and the system’s fans — will be paused. After the interaction, audio is resumed.

Functionally, this version of Siri has a few tricks up its sleeve. In addition to the wide range of tasks Siri can do on iOS, the Mac version can deal with files, locate content in your Photos library, create widgets and more.

For example, if I ask Siri to “Find photos of the ocean,” Photos.app will open and show me pictures of the ocean² in my local library:

However, if I say “Find photos of the ocean on the Internet,” Siri will return photo results via Bing, just like on iOS:

Images found via Siri can be dropped into applications like Keynote and Slack, but when dragged to Finder or even Messages, show up without file extensions and are all named “cr.” Drag a new one in, and Finder asks if should override or keep both, as the file names match.

Preview can open these images, but things like Quick Look don’t work quite right.³

File name bug aside, having this sort of content⁴ just a spoken command away is cool, but I don’t think it’s going to drastically change the way I work on my Mac.

However, for many users, Siri on the Mac is huge. Being able to talk to the Mac and retrieve information is a big win from the accessibility angle. I’m excited to see where that leads.

Siri + Files

Let’s get this out of the way first: Spotlight still exists in macOS Sierra, with all the same tools it’s had for years. For example, I can still search with Spotlight for “keynote documents” and see its results:

Now I can ask Siri to show me all of my Keynote documents:

There is one big difference between these sets of results worth pointing out. Spotlight can surface email attachments, while Siri can just show what’s in my user folder.

Siri + Notification Center Widgets

On the Mac, Siri results can be used to create Notification Center widgets. 

All conversations with Siri have a small button with a plus symbol. Clicking it opens Notification Center (which now sports a white theme to match iOS) and adds Siri’s results to the top of the stack of widgets.

Here’s the clever bit: the content of these is constantly being updated by the system.

This leads to all sorts of possibilities. Creating a widget during a sports game would keep the real-time score just a swipe away. Creating a Twitter search with a keyword can help you keep updated on what people are saying about your brand. The possibilities are nearly endless.

(I would love to see this come to iOS. Seriously.)

Personally, I’m using the feature to keep tabs on the time where several of my coworkers live. macOS’ built-in widget uses analog clocks, which aren’t as fast to read, so Siri’s time results are perfect.

If this sounds familiar, it should. Mac OS X Leopard introduced “Web Clips,” a feature to create Dashboard widgets from parts of a webpage.

That feature is still in Safari, and Dashboard somehow still ships in Sierra,⁵ but this method of having Siri return content from the web in real-time feels much more elegant.

I’ll be honest with you. In my month or so of using macOS Sierra full-time, the most I used Siri was for the screenshots above. I’ve always wanted to type to Siri on my iPhone, and now that it’s on the Mac, that feeling is even stronger.

While talking to something like the Amazon Echo doesn’t strike me as odd, talking to my laptop does. Having the option to shoot a quick string of text to Siri to decipher would not only be more comfortable, but probably faster for me as well.

I’m sure Siri will be a big deal for many users. It’s just not for me.

Continuity Features

Since the advent of iCloud, Apple has used the service⁶ to tie the Mac to its iOS-running cousins.

Continuity is the part of iCloud that forms a bunch of tiny bridges between the Mac and iOS devices, like shared phone calls and Handoff.

With iOS 10 and macOS Sierra, Continuity learned a few new tricks.

Auto Unlock with Apple Watch

Like other Continuity features, the premise is simple. If you have an Apple Watch that’s already authenticated as being on your body, why not use it to log in to your Mac?

The process is seamless. When presented with the login screen, the password field is replaced with a message saying “Unlocking with Apple Watch…”

On my Mid 2015 MacBook Pro, the process takes about two seconds. I definitely see it happening, but it is fast enough that I don’t second-guess that it’s working or wish I could just enter my password instead.

Once logged in, a notification is sent to the Watch:

This works when waking from sleep or entering from the screen saver. Logging in after powering on the computer, or logging in after going to the Login Screen from the Users menu bar item still requires entering a password.

Auto Unlock really makes me want Touch ID on the Mac. Having an Apple Watch be a requirement for a macOS feature is weird, and the fact an application like 1Password can’t use the Watch to unlock is a little frustrating. I’d like Apple to push the Mac forward in this area like it has the iPhone and iPad.

Universal Clipboard

Universal Clipboard is pretty straight forward: If you copy a URL on your Mac, you can paste it into an iMessage on your iPhone. Copy a photo on your iPad and paste it into a Pages document on your Mac.

This sort of feature could be a nightmare, but Apple has designed it to be intelligent.

First, it only works with devices within range of each other. If you leave your iPad at home, your spouse or kids can’t insert content into the clipboard on your Mac at the office.

Secondly, content is only transferred on paste. If you’re copying sensitive data, you don’t have to worry about someone else grabbing your iPhone and have immediate access to it. This does lead to the slightest hesitation as iOS pastes content, but I’ve learned to ignore the moment that elapses between tapping Paste and seeing copied content from my Mac appear on my iPhone.

Lastly, shared clipboard content is only available for two minutes.⁷ This helps make Universal Clipboard feel much more intentional. In my month or so of using it, I’ve never once felt surprised at my devices doing the “wrong” thing.

Universal Clipboard can be less than reliable, especially when going from a Mac to an iOS device, so your mileage may vary in practice. I trust a future update to either Sierra or iOS 10 will improve things.

This is one of the features Apple ships that feels like it was designed in a bubble. Universal Clipboard is great if you work in a very intentional way. If you’re at your Mac and go to pick up your iPad to finish a task, it’s great. If you share your tablet with someone else in the house, however, you can quickly be in a situation where devices in the same location are overriding each other’s clipboards.

Like other Continuity features, Universal Clipboard doesn’t have a toggle anywhere in System Preferences. If you’re signed into iCloud, the service is aware of your clipboard. That may be a deal breaker for some from a security perspective.

I think Universal Clipboard — and Handoff, etc — should be able to be toggled off.

iCloud Drive Desktop & Document Sync

Apple is finally taking on Dropbox.⁸ Kinda. Maybe.

iCloud Drive⁹ can now see beyond its own folder and can sync the contents of ~/Desktop and ~/Documents to other Macs logged into the same iCloud account.

(This can be enabled by going to the Apple menu, selecting About This Mac, clicking Storage, then selecting Manage.)

Right off the bat, let me say that I have very little interest in this feature. I use just one Mac for all of my work and non-work usage. Even so, almost all of my files are stored in Dropbox. If I were a multi-Mac man, I’d continue to use Dropbox.

That said, in my basic testing, I ran into no issues with this working correctly, but it could be slow at times. Syncing 800 MB of data between Macs on different networks¹⁰ took noticeably longer with iCloud Drive than Dropbox.

In addition to this content showing up on any other signed-in Macs, it’s accessible via iCloud Drive on iOS.

(All of this is assuming you pay for enough iCloud storage.)

All in all, you would expect the effect to be uncanny and transparent, just how Apple likes it, but some rough edges are showing.

For example, in your home folder, Desktop and Documents pick up Desktop — Local and Documents — Local as their names. Additionally, and perhaps more worryingly, Finder doesn’t always correctly report how much free space is actually available when these features are enabled.

I won’t be turning this on. I already have a system for syncing files to other Macs, and I don’t fully trust that iCloud won’t do something silly with my files.

Optimized Storage

Optimized Storage is one of those features that Apple’s marketing copy does a good job at simplifying:

Storage space maxed out? No problem. macOS Sierra can help make more room by automatically storing rarely used files in iCloud and keeping them available on demand. It can also help you find and remove old files you no longer use. So the files you’ve used most recently stay on your Mac and there’s always room for new ones.

According to its user interface, Optimized Storage can do two things to preserve free space on disk:

• Remove watched movies and TV shows in iTunes
• Delete “older” email attachments

iTunes media that are removed can be re-downloaded on demand, and Mail can pull attachments back down as needed. While those two bullet points may not seem like much, old content in iTunes and years of IMAP storage can really add up.

I’d be okay with this feature if that’s all it was, but in iCloud’s system preference pane, there’s more:

This list allows you to check or uncheck what iCloud-equipped apps are allowed to store things in iCloud Drive.

Optimize Mac Storage

However, that bottom item, “Optimize Mac Storage” makes things a lot more complicated:

The full content of iCloud Drive will be stored on this Mac if you have enough space. Older Documents will be stored only in iCloud when space is needed.

On the surface of it, this sounds great. Have a bunch of ancient Keynote documents and running low on space? iCloud will remove those from your drive, but keeps them available for download later. Finder changes the icon to let you know it has been removed from the local disk.

However, there is no control over what iCloud can and can’t remove, and no controls over what “enough space” means. If you are syncing your Desktop and Documents folders, the documents stored there could suddenly be optimized away if Sierra and iCloud decide you don’t have “enough” free space.

Not surprisingly, there’s no way to tell the system how much free space is okay to leave before the feature kicks in.

There’s no way to tell the system to “always leave these files on my drive” with any granularity. If you allow iCloud Drive to sync a folder or app’s documents, it can do as it wishes with those files.

Contrast this with Dropbox, which allows per-folder control of what is synced locally and what is stored the on the cloud. There are no surprises in this system. iCloud’s Optimize Mac Storage can get rid of local data without any real warning. If you get on a plane to work on something, the file could be gone.

No thanks.

Reduce Clutter

Beyond Optimized Storage, macOS Sierra offers a couple of other ways to manage disk space:

• Automatically empty the Trash every 30 days
• Reduce Clutter

The first option is pretty simple; the second is less so. Reduce Clutter presents the user with a list of large files¹¹ on their system:

Hovering over an item in the list will reveal controls to see the item in Finder, or delete it.

Deleting the file removes it from the system, bypassing the Trash. Clicking Remove on that sheet really does nuke the file from orbit.

While I understand why the feature works this way, I think it’s the wrong choice. Bypassing the Trash could be dangerous; as bad as the practice may be, some users see Trash as a safety net. I think a lot of users scroll though it thinking, “Do I really want to delete this?” before emptying it.

I’d be happier if Reduce Clutter would move items to the Trash, then prompt users to empty the Trash when they are done.

Like the iCloud Desktop and Documents sync, all of these features are found in System Information.app,¹² which strikes me as an odd place.

I have all of this stuff turned off, and don’t expect to visit this corner of macOS very often, if at all. I can manage my own disk, and I bet a lot of people will be fine without any of these options.

Apple Pay

Once my bank added Apple Pay, I became a convert. I have several stores I stop in at least once a week that take it, and I love not needing to take out my debit card — or expose its number — to make a purchase.

Until now, Apple Pay has been accessible via NFC on the iPhone, Apple Watch and in iOS apps. With Sierra, that changes.

This year, Apple introduced new APIs that run in native macOS, iOS and watchOS, as well as the ApplePay JavaScript framework, which incorporates the service in — and I’m quoting developer documentation here — “iOS and macOS Safari-based websites.”

Tough luck, Chrome¹³ users.

I can understand why Apple is limiting Apple Pay to Safari. While they probably could open it to other browsers, it wants to make sure it controls the whole stack. I think it’s similar to the thinking about NFC in the iPhone. It could be used for other things, but Apple wants to build a moat around its mobile payment system. I’m okay with that.

To use Apple Pay on the web isn’t as clean-cut as walking into a Whole Foods and buying a jar of organic peanut butter, as this dad joke from WWDC shows:

Thank God she didn’t own an iMac G3. That’ll put your back out.

Apple Pay on the web requires a nearby iPhone or Apple Watch.¹⁴ The payment process starts in Safari, but is then handed off to Touch ID on the iPhone or a double-press on the Apple Watch’s side button. Once that input is received, Apple Pay in Safari will complete the payment.

Of course, this little two-device dance wouldn’t be needed if Macs supported Touch ID hardware, but as of this writing, that’s still a dream.

Using Apple Pay on the web is fast, easy and secure, but is it worth switching away from Chrome? I’ll still use Google’s browser, but when I see an Apple Pay button, I’ll switch over to Safari for the peace of mind.

Updated First-Party Applications

Any time Apple updates an OS, some subset of first-party apps that come with the system see updates as well.

Photos

In Sierra, Photos.app has picked up many of the features found on iOS 10, including object identification and memories.

Object identification¹⁵ works the same as it does on iOS. Enter a search term, and Photos will return images with those objects or scenes.

In my testing, I get consistent results across my iPhone, iPad and Mac when looking for subjects in photos.

Apple is doing all of this indexing and searching on each device independently of the others. Apple’s willing to spend your hard-earned CPU cycles to keep this data off of iCloud servers. While at first I thought this was the wrong trade-off, in reality, Photos.app seems to do a good job at rendering the same results across devices.

Memories work in much the same way. My iPhone, iPad and Mac have the same main Memories, but do differ from one another once it comes to seeing related memories.

Beyond these features, Photos.app works and operates the same way it did under OS X El Capitan.

Messages

The headlining feature of iOS 10 is the blossoming of iMessage from a superset of SMS to a full-fledged, modern messaging platform complete with effects, apps and stickers.

Only a subset of those things have made their way to macOS Sierra, and it leads to a confusing, halfway broken experience for those of us in front of Macs all day.

Here are the three new things Mac users can do in Messages:

• Send “huge” emoji
• “Tapback” with a heart, thumbs up or down, a “Ha ha,” exclamation point or question mark
• Play video and preview links in-line

In case you were hoping emoji entry had gotten any better in macOS this year, let me rain on your dreams right now: it hasn’t.

Tapbacks are sent by right-clicking on a message bubble and selecting “Tapback…”

Mac users can see stickers, but can’t send them. Right-clicking on a message reveals an option to “Show stickers.” This previews the stickers in a pop-over:

Perhaps most importantly, the Mac can’t send or receive Lasers, or any of the other, inferior effects.

In the most anti-climatic bit of backwards compatibility ever, all Mac users see is a note saying:

(sent with Lasers)

What a buzzkill.

The worst part about this is that iOS will play any missed effects the next time you open a thread. For example, every time Casey Liss sends me Confetti, Lasers and then Balloons, I’ll get the above, depressing text alerts on my Mac, but when I tap Casey in iMessage on my iPad, the app will play Confetti, Lasers and then Balloons. In order. It’s very jarring.

The only exception is Invisible Ink. Messages received on the Mac using this effect are obscured until the cursor is rolled over them. However, Invisible Ink messages can’t be sent from macOS.

I guess Apple wants to keep incoming SECRET ADULT MESSAGES funny jokes safe from prying eyes, but assumes they always come from iOS users.¹⁶

As goofy as these effects and stickers can be, it would have been nice to see them come to the Mac at the same time. Messages is an important service to Apple, and having the Mac be a second-class citizen in it doesn’t feel very good.¹⁷

Console

It may not be anyone’s favorite utility, but Console is an important corner of macOS. The new version, according to Apple’s documentation, “displays log data from connected devices, supports tokenized searching and saved searches, and shows connections between related messages across multiple processes.”

So, yeah. There’s that.¹⁸

Notes.app

Notes got a huge update last year with El Capitan. This year, it gains two much-desired features.

The first: the font sized used for note content can now be made larger across the application.

Secondly, thanks to advances in CloudKit, notes can be shared with other iCloud users.

The sharing of a note is a slightly unusual process. After clicking the new share button in the app, it presents you with a bunch of ways to share the note itself:

Select a method, and then you’re prompted to share the note with a person:

After sharing, participants can be viewed and removed by pressing the same share button.

This is not like editing a Google Doc. You can’t see someone else typing, letter by letter, and there’s no indication of where their cursor is, or what they have highlighted.

That said, in my testing, I haven’t seen it do the wrong thing. When in doubt, Notes seems to leave all sides of a potential conflict in place; it doesn’t seem to remove content if it thinks there is a sync conflict.

I can live with that. While it’s not the fastest system in the world, I think Notes.app will be a great tool for things like shared lists that aren’t actively edited by multiple people.

Grab Bag

As with all major Apple releases, the company works in a bunch of non-headlining features that are worth talking about.

Tabs

In Sierra, applications that use standard UI elements can now take advantage of Safari-like tabs:

Tabs in Byword

Applications can turn open windows into tabs via the “Merge All Windows” command under the Windows menu. Additionally, the Dock system preference pane now has options to force applications to always create Tabs, create them when in Full Screen mode, or to never use them automatically:

By default, applications will only create tabs in Full Screen mode. I think that’s the right call. If you have Pages open in Full Screen, it only makes sense that creating a new document should keep you on that screen. I’m leaving the default option in place, as I often have multiple documents of the same type open at once that I need to quickly go back and forth between.

Picture in Picture

Like on iOS, video can now be played via Picture in Picture, as long as its on the web using the standard HTML5 video player. YouTube uses it own player, so PiP doesn’t work there.¹⁹

For video that is supported by the feature, a new button appears on the controls. Once clicked, the video pops out and can be dragged to any of the four corners of the display.

(Holding Command while dragging allows you to place the video in any location on the screen.)

It’s important to note that if you close the Safari window the video originates from, the video playing in Picture in Picture will also be closed. The browser will warn you of this when closing tabs that have spawned a PiP window.

Wide Color

In Sierra, Core Graphics, Core Image, Metal and AVFoundation have been updated for the wide-gamut color built into the Retina iMacs. I expect this tech to spread to other Macs over time, so it’s good to see Apple embracing it through more of the system.

APFS Developer Preview

Lastly, macOS Sierra comes with a Developer Preview of Apple’s new file system.²⁰ APFS comes with these limitations as part of the preview:

• An APFS-formatted volume cannot be used as a startup disk.
• Filenames are case-sensitive only.
• Time Machine backups are not supported.
• APFS-formatted volumes cannot be encrypted using FileVault.
• Apple File System cannot use Fusion Drives.

Unless you work on utilities that interact directly with the file system, there’s no reason to migrate from HFS+ at this point. APFS is expected to ship in 2017.

Conclusions

Without a doubt, the big story this year is Siri. While I’m not personally amped about it, many users will take to talking their Macs quickly. For some, it will make the Mac more accessible than it has ever been.

With improved Continuity features, Apple continues to make its platforms more aware of each other, and play more nicely together. Things like Auto Unlock and Universal Clipboard reward users who own multiple Apple products and bounce between them to get their work done. In a world where Apple ships multiple major platforms, these sorts of improvements are always welcome.

Years into the SSD revolution, Apple is finally giving Mac users robust tools to deal with small drive sizes, and iCloud Drive is finally taking on Dropbox. CloudKit has proven to be robust and trustworthy, and I hope these new features are just as good.

However, like Siri, I don’t anticipate using these features either. For me, macOS Sierra brings stability and some small niceties, but the headline-making features aren’t all that exciting to this power user.

If it seems like macOS Sierra offers less than some its predecessors, that’s because it does. In a way, it seems a little forgettable for someone like me. I think I’m okay with that.

macOS is a platform getting annual updates 15 years into its life. I don’t expect big, sweeping changes, and honestly, I don’t want the disruption in my workflow. Slow and steady is fine with me, and that’s the line Apple is toeing these days with macOS. In a release filled with features I really don’t want or need, I’m left feeling a little … forgotten.