macOS Sierra: The MacStories Review

The first thing that may catch the eye of many looking to upgrade their Mac this year is the demise of the classic ‘OS X’ moniker. The end of OS X has been long rumored, and the expectation has often been for the Mac to move to whatever Apple chooses to name their OS 11. This would of course be a change on a massive scale, such as that between OS 9 and OS X was over a decade ago.

This year, with OS X finally seeing the end of its reign, will we be seeing another epochal change in Mac history?

Nope.

After a decade of mispronounced Roman numerals, Apple is ready to let go of the name, but not the number. The full title for the 2016 iteration of the Mac operating system: macOS 10.12 Sierra. OS X may be gone, but OS 10 survives.

Since the mystical OS 11 didn’t come in the aftermath of the last big cat, didn’t come on the heels of version 10.9, and now again hasn’t come to usher out OS X, it’s starting to look like it may never come at all. Let’s all cross our fingers and hope that that’s true, because the bottom line is that OS 11 isn’t needed anymore.

These days, Apple is a very different company than it was when OS X made its debut. The Mac is no longer Apple’s darling. It was long ago pushed aside by the iPod, then the iPhone and iPad, and now even a watch and a TV box. Each of these is its own platform, running its own operating system. Each of these has its place in the new age Apple ecosystem.

With iOS, watchOS, and tvOS all around, the freshly renamed macOS no longer serves the role of scrappy upstart. Today, the Mac is the eldest platform, and macOS needs to focus on stability and productivity. Leave the epochal changes to the young guys.

With this year’s update, named after California’s Sierra Nevada Mountain Range, macOS builds once more upon the strong base of its many predecessors. Trenchant in its restraint, 10.12 shirks sweeping changes in favor of iterative improvements. A perfect example of an update to a mature operating system done right.

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Siri

I’m not sure that Siri has ever been particularly high on anybody’s wish list for a macOS (or OS X) update. And yet, it’s always just felt obvious that it would only be so long until Apple’s intelligent assistant made its way to their desktop operating system. This year, Siri has finally made the leap.

Siri on the Mac is focused mostly on multitasking. This is a big digression from the iOS version of Siri, which consumes the entire interface and does not allow you to do anything else until an interaction is finished. Despite this fundamental change, macOS Siri is more or less just a port of its iOS version, with only a few new tricks and special features.

Apple thinks Siri on the Mac will be useful when you want to take care of something quickly while you’re still in the middle of something else. The example they use on their website shows a user asking Siri to look up nearby restaurants while they are in the midst of messaging with their friends.

On the Mac, where opening an app feels like a lot more overhead than it does in iOS, I do see uses for Siri in situations similar to the above example. The intelligent assistant’s interface is light and fast. It can search Maps quickly without opening the Maps app (until you need to), it can rapidly get a certain playlist going without requiring you to navigate the iTunes interface, and it can easily send texts without you context switching to the Messages app.

Siri does more than this, too. The assistant on the Mac is very into files. You can ask Siri to show you all the files you’ve worked on in the past day or week, or show you the contents of a certain folder. You can then refine results based on data in the titles.

Once you have a certain search that you’d like to save, you can pin it to Notification Center for easy access. This can be a certain folder of files on your computer, or it can be something like sports scores or nearby restaurants. Any query that Siri for Mac returns shows up as a card that can then be pinned. Pinning cards simply requires clicking the + button in their upper right corner, and to remove them later just hit the x button in the card’s upper right corner in Notification Center.

The contents of Siri searches can also be manipulated via drag & drop. If you drag the border of a Siri card, you will pull a PNG screenshot of the results which you can drop in a folder or app. If the contents of the card are draggable, such as images that show up when you ask Siri to do a web search, then you can drag those around like standard files too.

Some other useful options: ask Siri to find certain photos in your Photos library, how to spell certain words, or how much free space is currently on your Mac. All of these will return results as cards.

Siri can be activated in several different ways on the Mac. There’s a new menu bar item to the left of Notification Center which will activate Siri, and there’s also a new Dock icon to call on the assistant. Finally, you can hold a key command. The command defaults to holding Option-Space, but can be changed to holding Command-Space or pressing Fn-Space, or to a custom shortcut of your choosing.

The shortcut can be edited in the new Siri section of System Preferences. This is also where you can go to change the language and voice of Siri. You can even pick which microphone you want Siri to listen from, and whether or not you want Siri to give voice feedback in response to commands. Finally, you can disable the menu bar button or disable Siri entirely from this preference pane.

I enjoy the idea of Siri on the Mac in the same way I enjoy the idea of Siri on the iPhone. The ideal of having an intelligent assistant to quickly help out with various tasks is a great one. In practice, however, I find I use Siri on the Mac even less than I do on iOS (and I rarely use Siri on iOS).

While I think that a lot of the features Apple has built for the macOS version of Siri sound useful, the reality is that talking to your computer just isn’t all that practical in most situations. I’m usually at my Mac in the office where I work or in a coffee shop. Neither of these places are great for talking out loud to a computer. When I am on my Mac at home, I’ve still found that it’s easier to just take care of most things manually. I move fast on the system, often faster than Siri would be able to anyway — particularly for file-related functions.

Ultimately, I’ve found Siri on the Mac useful a few times to run a quick search in Maps or start a certain playlist. I think the assistant could have had more to offer if Apple had given it a textual interface so I didn’t have to talk out loud to my computer. Even then I might find manual methods more natural.

I’m glad Siri is on the Mac; it seems like it should be since it’s on all of Apple’s other platforms. Despite that, though, I don’t think I’ll use Siri very often, if at all.

Universal Clipboard

The new Universal Clipboard is probably one of my favorite features of the macOS Sierra update. The feature uses Apple’s Handoff framework to sync the clipboards of all of your Apple devices together. Copy some text on your iPhone while you have your Mac open, and you can paste it on your Mac. The same thing works from Mac to iPhone, from iPhone to iPad, etc.

When I first heard about this feature, while I was excited for the utility, I was also a bit apprehensive about my devices overwriting each others’ clipboards. Data loss is never fun, even on the (generally) small level of what’s on your clipboard. Sometimes I will copy something important on my Mac, particularly while at work, and I’ll want access to that a bit later. If I pause for a moment to do something unrelated on my iPhone, and happen to copy something while I’m doing so, I wouldn’t want to lose my Mac’s clipboard. Thankfully, after three months of testing macOS Sierra and iOS 10, I’m happy to report that I have never had a single issue of that nature with the Universal Clipboard feature.

“Universal Clipboard” is a somewhat misleading name. It sounds great as a marketing term, but it implies that all of your devices are now going to have one single clipboard, probably held in the cloud, which they all constantly write to and read from. Thankfully, this is not how the feature works.

All of your devices continue to have their own independent clipboards, and in day to day activity on any one device it will work exactly as it always has. The change comes along only when all of the following points are true:

You have more than one device unlocked and on at the same time

You have recently copied something on one of the devices

You paste on a different device shortly after copying on the other

At this point, the device that you have pasted with will reach out via Handoff to get the data that you copied on the other device. It is only doing this because the other device is unlocked, in range of Handoff, and has recently copied something onto its clipboard. Once it has transferred the data, which can sometimes take several seconds, it will paste it for you.

If you copy something on one device, then lock that device, then paste on a different device, nothing special will happen. Universal Clipboard only works when Handoff has an active connection between devices (and a device has copied recently before another pastes).

I’m not certain if there’s an exact timeout on when one device stops broadcasting that it has something to paste over Handoff, but if you lock a device and then unlock it, it will no longer present its clipboard to be pasted from, even if the Handoff connection is active.

We can go over the technicalities and specifics all we want, but when it comes down to it, Apple seems to have nailed down the user behavior for this feature. Like I mentioned at the beginning, I’ve been testing these systems on my main devices for three months now, and not once have I had the Universal Clipboard feature cause an unintended paste from another device, or overwrite a clipboard that I wasn’t intending it to overwrite.

I’m often bothered by Apple’s determination to take on complex features without presenting an actual interface. For instance, I never generate passwords via the Safari password suggestion feature because there’s no easy way to then see that password if I ever need it on a non-Apple system. Instead, I use 1Password, which has a fantastic interface to easily get my passwords if I ever need them.

Clipboard sync services and clipboard managers are not new concepts, and every one I’m aware of has an interface of some sort. Apple’s, like their password system, has no interface whatsoever. Apple wants Universal Clipboard to be completely invisible and “just work”. I don’t say this often about these kinds of cloud-controlled software initiatives from Apple, but in this case, I think they’ve gotten it right.

Universal Clipboard isn’t perfect. It could stand to be faster (if you tap on an iOS device and don’t see the Copy/Paste/Look Up menu come up right away, that delay might be from Universal Clipboard), and I wouldn’t complain about some sort of way to re-summon overwritten clipboards on those rare occasions when it might go wrong. Overall, the feature has provided me with nothing other than convenience.

I now have an answer to the “what’s the best way to get this text from my iPhone to my iPad immediately” problem. I just copy it on my iPhone and paste it on my iPad. No more texting or emailing myself things, and that’s fantastic. Universal Clipboard even works with photos and other types of media, although you’ll have to give it a bit longer to transfer the data between devices.

In an OS update that is made up mostly of small-but-nice improvements, I think Universal Clipboard is the best of them all. It’s not a total game-changer, but it’s a seemingly little thing which greatly speeds up a task I have to do on a regular basis. It brings the Apple ecosystem in closer, and blurs even further the lines of the differences between individual devices.

Auto Unlock with Apple Watch

I covered this feature on my watchOS 3 review already, but suffice to say, I didn’t find Auto Unlock with Apple Watch to be quite as exciting as I was hoping. When I first heard the new feature announced at this year’s WWDC keynote, I think my mind ran away from me a bit. I was envisioning a Mac that no longer had the burden of a login screen. Instead, it would be unlocked automatically based on the presence of my Apple Watch before I even got to it, and when I walked away it would also automatically lock.

In reality, this isn’t quite the way it works. In my testing, the speed of connection between my Apple Watch and my Mac weren’t fast enough to make the feature very useful. At the login screen I’ll get a spinner telling me the computer is unlocking, and a second or two later it will unlock. As I wrote in my watchOS review, a second or two of doing nothing but waiting is even worst than the time it takes to manually type in your password to get logged in (which would probably take barely longer than this anyway).

Further promoting my disappointment in this feature is that the Mac does not auto lock when the Apple Watch leaves the area. I’m not sure why this isn’t an option, as it seems almost more useful to me than using the Watch to unlock the Mac. I love the idea of no longer having to worry about whether I forgot to lock my Mac when I walk away because I know my Apple Watch will have taken care of it.

Sadly, auto lock is not in the cards this time around, and auto unlock does not yet have the speed it needs. I’ll keep hoping for a future update with auto lock, and I’ll be looking out for these rumored new MacBook Pros with Touch ID to take care of the inconvenience of unlocking my Mac.

iCloud Drive

With macOS Sierra, Apple is expanding iCloud Drive syncing from a single folder to three different folders. Alongside the iCloud Drive folder, the new update will now sync the Desktop and Documents folders from your Mac into iCloud as well.

This has some fairly wide-reaching benefits. According to Apple — as well as all the anecdotal evidence I’ve ever known — people store most projects that they are currently working on either on their Desktop or in their Documents folder. Thus, by syncing these folders into the cloud, Apple is allowing access to your current important projects from all of your devices. Furthermore, iCloud now provides an automatic offsite backup to these important files by holding copies of them beyond the local ones on your computer.

This is a pretty simple and straightforward feature with clear benefits. The only downside is that if you are still holding onto that 5 GB free iCloud tier, you’ve almost certainly got a decision to make now. Personally, I think it’s worth it just to get another backup of my most important files, and with the added bonus of having access to them everywhere.

In classic Apple style, there’s no real interface to these new iCloud Drive features. I think it would be very nice to be able to specify exactly which folders on my Desktop should be stored in the cloud and which shouldn’t, but there is of course no such option. The only choice that you have here is to turn Desktop and Documents syncing on or off, which can be done through System Preferences -> iCloud -> “Options” on the iCloud Drive row. The setting is on by default.

Apple Pay

With macOS Sierra, Apple Pay is finally coming to the Mac! …Sort of. In the absence of a proper way of ensuring your identity via your Mac, Apple Pay for Mac just initiates payments and then kicks them off to your iPhone to get validated via Touch ID. With that in mind, the real feature here is less Apple Pay for Mac, and more Apple Pay for the web.

Websites can now integrate Apple Pay as an option for checkout in their online stores. If you are checking out of such a store and your Mac is aware that your iPhone is nearby, it will notify the website that Apple Pay is an option. In turn, the website can display the Apple Pay button to the customer, and tapping that button will initiate the payment on their iPhone.

Websites with Apple Pay integrations have been tough to find prior to launch day, so I’ve thus far been unable to test how functional this exchange is. I’m not sure if it works over Handoff, which would require your iPhone screen to be on in order for the communication to work; or some sort of push notification process, which seems like the best option since it would work regardless of your phone’s screen being on. It could be a combination too, using a push notification to ping the phone, then handling the transaction via Handoff once the phone is on and the customer has accepted it.

I’m sure we’ll find out soon once websites start to release support for the new feature. Personally, I think it will be a fantastic boost in website checkout experiences. Even with Auto Fill handling most of the information fill-ins these days, it’s still a pain to have to double check things and fix mistakes caused by poorly coded forms. Being able to just hand this off to Apple Pay, where I know the transaction will be secure and I know my information is correct, is something I’m very excited about.

The last aspect to touch on here is that it’s hard to think about this feature and not feel like those rumors about Touch ID on the Mac are vindicated. Passing the process off to the iPhone is fine, but its certainly not the best process. It precludes any Mac users who are not iPhone owners from having access to a great feature, and it complicates the process of making the payment by involving wireless technologies that are not 100% reliable. We’ve all had the experience of trying to AirDrop between our Macs and our iPhones and having them inexplicably be unable to see each other. If they’re using a similar technology (if not the very same one) to determine when the iPhone is in range, the feature may end up not being enabled at certain times when it should be. All of these problems could be immediately relieved if the Mac could just handle the identity validation on-device.

Optimized Storage

Optimized Storage is a new feature that makes some people nervous, but I personally am a big fan. In macOS Sierra, Apple scans the data on your computer and determines which files you don’t need locally on the machine when you run low on space. Mostly, this consists of large old files which you haven’t touched in quite a while.

When space is needed, macOS Sierra will automatically offload these old files to iCloud. This clears room on your hard drive without requiring you to delete any of your files.

The obvious caveat here is that if you ever do need the file, you now have to download it back to your machine before you’ll have access to it. This means that if you don’t have an Internet connection when you need the file, you won’t be able to get it. Similarly, if the Internet connection you are on is not very fast, it could take a very long time for a large file to redownload to your computer.

I think this is a case where everyone will need to evaluate their own use cases before deciding on this feature. Personally, I know I have a lot of big old files on my computer, none of which I really want to delete, but also none of which I ever really use. In the past, I’d offload some of these to an external drive, but to me, this new Optimized Storage features sounds perfect. Rather than removing the files completely, I can still have them pretending to be there, but they won’t take up space unless I ever need them again. Furthermore, I will then be able to get them no matter where I’m at, rather than needing to retrieve my external drive in order to transfer them back to my machine.

If you compare the Optimized Storage feature to moving things to an external drive, I think it makes a lot of sense. If you’re only comparing things being on your computer vs things not being on it, then obviously things being on it is better. The main thing to keep in mind, though, is that Optimized Storage will only remove files if you run low on space. In other words, when Optimized Storage starts removing files is when you would have had to start finding things to delete anyway.

Once again, Apple makes their feature a little less useful by refusing to provide an interface for it. I think there would be a lot less trepidation about this feature if we had the ability to choose exactly the files that are transferred. Unfortunately, we (mostly) do not.

I say mostly there because it is possible to manually retrieve files which have already been transferred to the cloud. Any files that have been moved from your computer to the cloud will include a small download icon on their right side when you look at them in Finder. Just click the download button to redownload a file to your machine. Beyond that, there’s not really any other interface for the Optimized Storage feature. You can’t pick the files to offload for it – it just takes care of this by itself.

For my situation, I think Optimized Storage is exactly what I’ve been wanting. I have old files on my Mac, but I rarely need to access any of them. Furthermore, 99% of my Mac usage is done while on a decent Internet connection, so I don’t think downloading something that I suddenly need would ever be much of a problem. With this in mind, if Sierra wants to take over the task of having to figure out which files should stay and which should go, I’m all for it.

I think it’s important to note that Optimized Storage is on by default when you install macOS Sierra. On the one hand, if Apple is confident enough in the feature to enable it by default, I would expect it to be quite solid and not cause problems for the great majority of users. On the other hand, if you read all of the above and still feel that you don’t want the feature messing with your storage, then you should probably turn it off. You can do so from System Preferences -> iCloud -> “Options” in the iCloud Drive row -> uncheck Optimize Mac Storage.

Photos

The Photos app in macOS Sierra has received a nice new set of features. Most of these are making use of what Apple is calling “computer vision technology” to run powerful object and scene recognition on your photo library. The results are impressive, and are being used in a few of the new features that have been added to Photos.

Memories

The biggest new addition, based on Apple’s announcement of the update at WWDC, is Memories. Memories is an attempt to intelligently gather together groups of related photos and videos into a “memory”. The goal is to allow you to relive certain events or periods in your life through the photos and videos you took of them.

Each “memory” will have a label such as ‘Best of Last Month’, and consists of a slideshow and a set of photos and videos. Double-clicking a memory will open it, showing the slideshow at the top and a summary of the photos making up the memory below. Memories will try to pick the “best” of all the photos that are drawn into the period. A Show All button will allow you to expand the summary of the memory to show all of the photos and videos included in it.

Underneath the photos and videos of the memory, you’ll find a ‘People’ section, which includes any people that Memories has determined to be in the photos above. The people displayed come from the new People feature in the app, which I’ll discuss below. If Photos has not identified anyone, this section won’t be present.

Below the People section you’ll find a map showing all the places where photos and videos from the memory were taken. Below that is a “related” section, which will show even more memories that you can look at.

At the very bottom of the page you’ll find options to delete a memory completely or add it to your “favorite memories”. The latter will create (or add to if you’ve already created it) a new “Favorite Memories” album, where you can see all the memories you’ve marked as favorites.

While Memories isn’t a feature that I use very often, I’ve been impressed by what it has surfaced over the last few months. Memories seems to generate new content sporadically, so if you check in every couple of weeks you will likely see new entries popping up (depending on how often you take pictures). I haven’t found the slideshows particularly compelling, but the groupings of photos and videos have been a fun way to look back on old times when I’m in the mood for that kind of thing.

People

The next “new” feature of the Photos app is the People section. While Apple is billing this as new, it’s really just an updated version of the Faces feature which has been in Photos since its beginning. If you have ever done any work to categorize pictures in Faces in the past, those have all been moved to here.

At the top of the People interface you’ll find a grid of people you’ve marked as “favorites”, and below those is the grid of the rest of the people that you’ve defined. When you double-click a person’s entry, you’ll open up an interface similar to Memories, showing all the photos of the person at the top. Below these will be a section showing other People present in the photos, below that a Places section showing where the photos were taken, and below that a Related section showing more Memories.

At the very bottom of the page are options to confirm additional photos of this person, favorite or unfavorite them, or add the entire group of photos of them as a memory. That last option will create a new entry in the Memories section of the app which is titled by the name you gave the person in the People section, and opens to the People interface.

If you select the ‘Confirm Additional Photos’ option, Photos will initiate a search of all of your photos looking for the person in question. This shouldn’t take more than a minute or two, but I’ve seen it get stuck a few times. If it takes longer than that to display the first photo, try hitting ‘Done’ in the top right and then hitting the button again.

Once it works, you’ll see photos show up one at a time, with a highlight circle around one of the faces in the photo. You can confirm whether the face has been correctly recognized by choosing Yes or No at the top. Keep choosing until you’ve gone through all the photos the app has recognized, or hit Done whenever you want. Also of note is that if the app gets a face wrong but you click Yes or hit return before you realize it, you can just hit Undo to go back to the previous photo and fix the mistake.

Adding new faces to the People interface is done at the bottom of the main interface, underneath the grid of current People. Clicking the plus button there will display a grid of recognized, but not yet categorized faces. You can then select one face and choose ‘Add’ to create a new Person based on that face, or select multiple faces and choose ‘Merge & Add’ to combine all of them into one new person. Once you’ve added a new person you’ll be back on the main People interface, and can then click underneath the new addition to add a name. If you already have another entry for the person you’ve added, just give them the same name (it should appear in a drop down as you type) and Photos will ask you if you’d like to merge the new photos into the existing Person entry.

Photos will automatically select a group of photos that it thinks is of the person in question when you create an entry for them. The more Photos you manually select when you add the original entry, the more photos the app will connect to that Person. Similarly, when you confirm a batch of photos of someone within the Confirm Additional Photos interface, the app will connect more photos than just the ones you confirmed. Every photo added increases Photos’ knowledge and ability to accurately add even more.

In playing with the interface, I’ve found that Photos seems to be fairly conservative with its guesses for confirming additional photos of people. It rarely proposes a photo that is not of the person in question, but because of this it also seems to miss a lot of photos of that person that it isn’t sure enough about. The best way I’ve found to get through this block is by adding another batch of photos that you select manually of the person, then merging those into the existing entry. This gives Photos more data to work with, and in turn it will start proposing more photos for you to confirm.

Overall, I’m not sure whether the facial recognition algorithm behind the People feature is any better or worse than the one behind the Faces feature last year (I’m pretty sure it’s at least somewhat different due to Apple’s computer vision technology being a brand new thing, but it’s hard to know for sure without someone in Apple telling us). At the very least it is comparable. Still, the interface for the People feature is a significant improvement over the clunky Faces interface from last year, and makes adding and merging new batches of photos for the same person far easier. Since compiling as many faces as possible for each person is pretty much the whole point of the interface, I give this section of Photos a big thumbs up compared to its old implementation.

Places

The new Places feature has been mentioned several times above, but basically consists of a new map interface that can now be found all throughout Photos. The Places map exists within the Memories and People interfaces, and will display the locations on a map of every photo in the selected memory or of the selected person, respectively.

If you open up any particular photo from anywhere in the app, you’ll see a Details button in the top right corner, and clicking on this button will show all the data about the photo. This includes which People the photo has been found to contain, as well as the Places map that will show where it was taken. In the top right above the map will also be a Show Nearby Photos button, which will inflate the map interface to fill the Photos screen and display all the pictures taken nearby to the photo that was selected.

Places is not really a new feature for Photos, as previous versions did separate groups of pictures by location as you scrolled down through your All Photos view. The utility of Places, however, is in exposing that location data in a far more prominent way than it was before. Now you can much more easily see a great visual representation of where your photos were taken, and it is more or less ubiquitous throughout the app.

Search

The final feature of Photos is the one I find to be the most useful. The search functionality of the app has been greatly improved in quality as well as in scope. This is where that fancy “computer vision technology” is truly coming into play.

The new search in Photos for macOS Sierra allows you to search for the content of your photos rather than just the metadata about them. For instance, if you want to see all of your photos that include trees, just search for ‘Trees’ and you’ll get them. This kind of computer vision is extremely difficult to pull off, but Apple has done a fairly decent job of it here.

When you first install macOS Sierra and open up the Photos app, it will scan your entire Photos library and start running algorithms and calculations to parse the objects within all of your photos. You should note that this process can take quite a while (hours or even days, depending on the size of your library), and these features will not be functional until it has been completed.

Once the process finishes and your pictures are ready to search, it’s worth noting that you can’t search completely freely. Rather, your searches are limited in scope to the categories that Apple’s scanning has identified within your photos. By extension, any categories that Apple does not scan for simply will not exist.

When you type in a search term, Photos will start showing suggestions for what you might be typing. If you type something that doesn’t exist as a category, you’ll get “no results” and be unable to run the search at all. When you do search for something that Apple has scanned for and found, you’ll see all of the photos that match the term shown in the window below. Unfortunately, there’s no way to see a list of all of the available search terms for your photos. As such, you just have to guess and check and see if the term is there.

In real world usage, search is at its most useful when there’s a specific photo that you’re trying to find. The hard part now is training yourself to remember that the feature is available. I’ve had multiple times over the last few months where I want to find an old photo and I spend forever looking for it manually, only to remember at some point after I’ve found it that I could probably have just run a search and surfaced it in seconds. If you think of search first and the photo isn’t categorized by anything you search for, you’ve only really lost a few seconds. If the photo does show up from the search, you may have just saved yourself several minutes of time for that single task. It’s a very powerful tool when it works right. Based on my own personal library, while it isn’t 100% accurate — or really even close to that — it’s accurate enough as to be a very useful tool.

Overall, Photos for macOS Sierra packs some interesting new features which push the application forward. This year’s update to the app focuses strongly on surfacing new data from our photos that was previously much more difficult to find. We can discover old memories, more easily compile photos of particular friends and family, and see exactly where we’ve taken our photos. We can even search for objects within them. As far as year-over-year updates go, this one seems like about as much as we could ask for.

Messages

Messages in macOS Sierra did not get nearly the overhaul that its iOS counterpart did this year. In fact, the only changes that the messaging app received were the bare minimum amount to keep it capable of understanding messages sent from iOS users.

The updated Messages app is capable of receiving sticker messages coming from iOS devices, and it does its best to place them in the same way that they were placed by the sender. In my experience, between my iPhone, iPad Pro, and MacBook Pro, the MacBook has been the only one to sometimes have issues with misplacing stickers by short distances. Even a short distance can completely change the purpose of the sticker, so that aspect is a bit disappointing. I hope future updates will get the scaling worked out to place stickers with higher accuracy.

Sadly, Messages for Mac has no support at all for placing stickers on Messages. It’s not surprising that iMessage Apps aren’t going to run in the Mac version of Messages, but I see no reason why sticker placement should not have been built-in.

Speaking of features missing despite no technical limitations, Messages for macOS neither has support for sending nor even viewing messages sent with bubble or screen effects. The Messages app in iOS 10 has a whole set of effects that can be applied to sending messages, such as having them appear with lasers or balloons behind them, or having them “slam” into place when they’re received. Messages for macOS has no support for sending messages with these effects, but even weirder than that is the way the app receives them. Messages knows when it has received a message sent with a bubble or a screen effect, but rather than displaying the animation, the app instead just shows the message regularly and then adds a parenthetical underneath it describing what effect it was sent with. “(sent with Lasers.)” or “(sent with Slam Effect)” are examples of what it might say, but it varies based on the effect that was used.

The only effect that does work on Messages for macOS is the “invisible ink” effect, which obscures the text with sparkles that can then be moved out of the way to read it. On iOS, you clear the way by swiping across the message or tapping within it. On macOS your mouse just acts like a finger, and sliding over the message will reveal its contents.

The final new feature of Messages is the only one that works for sending as well as receiving: expanding links inline. If you send or receive a URL in Messages for macOS, the OS will grab the contents of the website or video behind the URL and expand a preview of the page’s content inline right in the app. If the link is to a video from a supported website, such as YouTube, the video will be available to watch directly within the confines of the Messages app. This is a great feature which other messaging apps like Facebook Messenger and Slack have had for a long time. It’s great to see it finally make its way to Apple’s messaging platform as well.

That’s it for Messages for macOS Sierra. With all of the fanfare and excitement over Messages for iOS 10, I was expecting quite a bit more from the desktop version. At the very least, the app should be able to play screen and bubble effects, but I think that the Mac should also get access to sticker packs and be capable of placing stickers. I hope Apple brings Messages for macOS back up to date quickly. I would hate to see their messaging platforms diverge when one of their greatest strengths has always been the availability of the same features across all Apple product lines.

iTunes

At this point, it’s starting to seem like no major update of Apple’s desktop operating system will be complete without iTunes getting some sort of slight design refresh. macOS Sierra is no different, marking another year in which the behemoth of an application continues to drag along, devoid of the disassembly that it sorely needs. For this year’s new paint job and minor feature bump, Apple has placed the spotlight on the Apple Music section of the app.

iTunes works more or less the same as it did last year, but now the For You, Browse, and Radio sections of the app have been updated to reflect the same new design language as the iOS 10 Music app. Mainly, this consists of extra bold headlines and large artwork.

If you’re an Apple Music subscriber, the For You tab has two interesting new playlists now placed prominently at the top of the screen: My New Music Mix and My Favorites Mix. As a whole, I haven’t been particularly impressed by Apple Music’s algorithmic and curated “for me” content over the last year. These two new algorithms, however, are a different story.

The My Favorites Mix seems to pick very close to the standard set of favorite songs that you listen to. In my experience, it’s been including about 60-70% songs that I listen to on a regular basis. The rest are all songs I do not listen to but which are by artists that I do listen to. I’ve been very much enjoying this playlist because it stays within my comfort zone while still branching out the scope of songs I listen to by my favorite artists.

The My New Music Mix playlist also takes your favorite songs into account, but in my experience it doesn’t include any of those songs themselves. Instead, it clearly tries to branch out a bit further than the My Favorites Mix. In the last few weeks of using this playlist, I’ve found that it generally contains about 25% artists that I listen to (although always different songs from them than I generally listen to) and 75% completely new music. It doesn’t hit the sweet spot quite as directly as the My Favorites Mix for me, but it’s not supposed to. By definition, this mix is supposed to help us find new music, and it’s not going to be able to do that without sometimes picking songs that we don’t enjoy. That’s what the skip button is for.

Back to iTunes, below the two new Mix playlists you’ll find recently played albums, followed by daily featured playlists and albums, then artist spotlights, and finally new releases at the very bottom. Overall, I like the new For You interface: it’s a lot more straightforward and less cluttered than the previous version. I’ve found myself going to use it more in this new update than I did throughout most of last year (on my Mac and on iOS).

If you’re wondering what happened to the Connect tab, it isn’t gone entirely. It has simply been demoted to a sub-section of the For You interface. At the very top of For You there are two tabs now. The default Recommendations tab has all of the above which I already touched on. Next to it is the Connect tab, which contains a grid of cards making up posts from any artists you follow.

Beyond For You, the Browse tab does what its name suggests. It has five tabs itself: New Music, Curated Playlists, Videos, Top Charts, and Genres. All of these are more or less self-explanatory, and nothing has changed since last year except for the bolder design that is seen across the Apple Music UI. The same can be said for the Radio section of the app.

Overall, the most interesting aspect of the changes to the Apple Music sections of iTunes are the introduction of the Mix playlists. If you check out nothing else about the new iTunes refresh (and you’re an Apple Music subscriber), make it those two weekly playlists. I’ve already found several great new songs and artists that I hadn’t known about in just a few weeks of the playlists being out.

Beyond Apple Music, the other big new feature of iTunes in macOS Sierra is the addition of official lyric support in the interface. Lyrics can be found via the Up Next/History button, which now has a new tab added for them. While iTunes will not be able to identify lyrics for every song, when it can find them it shows them in the popover window.

If you’re controlling your music via the iTunes MiniPlayer, you can see lyrics there too, although they’re a bit hidden. First, you’ll need to click the “…” button to open the dropdown menu, then from there choose ‘Show Up Next’. This will expand the MiniPlayer downward to display the songs coming up next, and you can then click the dropdown arrow next to ‘Up Next’ and change it to ‘Lyrics’.

The last step there might not be necessary, because the MiniPlayer’s selection will mimic that of the main iTunes window selection for Up Next, History, or Lyrics. However, regardless of which is shown or hidden, the button in the dropdown menu will always read ‘Show/Hide Up Next’.

iTunes does not have any fancy features for their lyric integration, such as highlighting which line is currently playing in a song as it goes. This is one advantage that user-driven services such as Musixmatch have over the first-party lyric features. In my personal experience, Musixmatch also seems to have a more comprehensive library of lyrics than iTunes does at this time.

Regardless, it’s great to have official lyric support in iTunes. I’m sure Apple will improve their database over time, and maybe at some point we’ll start to get more advanced features like those offered by other services.

The new iTunes update in macOS Sierra is fairly minor overall, but still manages to bring some nice improvements. Lyric integration is great to have in the official music app for macOS, and the new Mix playlists are fantastic additions for Apple Music subscribers. The new For You section in general is a bit more coherent too, which I appreciate.

At some point in the future, it feels like Apple will have to handle the unbundling of iTunes’ myriad of parts. The application now contains the interfaces for on-device music, Apple Music, iOS device syncing and management, the iTunes Music Store, the iTunes movie and TV show stores, Apple’s podcasts directory, the iOS App Store (yeah, that’s still embedded in iTunes, too), burning music onto discs, iTunes U… I could keep going, but I think you get the point. The application is very good at hiding all of these parts so that it doesn’t look as complex as it is, but all that really does is make it harder for people to find other features when they need them.

Someday, I will feel great satisfaction and joy as I finally get to write the story of The Great iTunes Deconstruction. Today is not that day.

Tabs

Here’s a new feature which will bring enjoyment to any tab lovers out there. In macOS Sierra, most document-based applications which have the ability to open new windows will now also have the ability to open those windows as tabs. Interestingly, the feature is going to work automatically for many third-party apps, requiring no work from their developers at all.

To control the tabs feature, there is a new setting in the Dock section of System Preferences. The default is to always open new windows as tabs when apps are running in Full Screen mode. You can choose instead to always open new windows as tabs (where possible) even when not in Full Screen, or to only ever do it manually. Most apps will allow this manual behavior through the familiar Command-T command, or if not then through the File menu. If it isn’t an option in the File menu, the app likely does not support the new behavior.

This isn’t a particularly far-reaching feature, but it’s nice to have choice for anyone who prefers the interface of tabs over that of new windows. Personally, while I think tabs are great for web browsers, I prefer separate windows most of the time for other apps. That said, if I ever do run an app in Full Screen mode, creating new windows as tabs is a far better experience than the alternative, which will create an entirely new Desktop for the window and then show a slow Desktop sliding animation as you transition over to it.

The actual interface of tabs in these apps is exactly what you’d expect from Safari, Terminal, and other apps that already had tabs. Most of the time, the standard key commands for moving amongst tabs still work (this may not be true in third-party apps which have assigned those key commands to other features), and dragging tabs around to reorder or create new windows from them has the same behavior as you’d expect.

Picture in Picture

Picture in Picture is an extremely welcome new feature in macOS Sierra. It comes in the form of a new button which shows up in the bottom right corner of supported video players.

Clicking on the button causes the video to pop out of its window into a smaller rectangle, which then floats on top of other content. The rectangle’s size can be adjusted manually to a maximum of a little less than 1/4 the size of the screen (on a 13” MacBook Pro). Moving the box around will cause it to snap to one of the four corners of the screen. If you want it to stay exactly where you place it without snapping, you just have to hold down the Command key as you move it.

There’s not much else to Picture in Picture. It is a simple feature that gets its job done well, and I’m excited to have it coming to macOS. I’ve been using Picture in Picture on my iPad Pro for nearly a year now, and it’s a great way to watch video while doing other tasks.

The last thing to discuss here is compatibility. While many websites will have the Picture in Picture button inserted by default into their video players, others will not. Unfortunately, websites which use customized video players, such as Netflix, are not going to have the Picture in Picture option without building support for it themselves 1. This means that we’ll have to rely on the developers of these websites to put in extra work in order to support the feature. Based on how long it has taken for iPad Picture in Picture support to be built into many apps, I wouldn’t expect these companies to move quickly here either.

Conclusion

macOS Sierra is not a game-changing update. It is an iterative improvement to the solid structure that is Apple’s desktop operating system. This is an operating system that is mature enough to only need such iterative improvements from here on out, building slowly on what came before and choosing carefully where it wants to go next.

Sierra proposes several brand new routes for the next steps of this operating system. The iCloud Drive improvements show Apple’s first moves toward a possible future where Macs can be backed up to and restored from iCloud as easily as iOS Devices. Optimized Storage is a glance in the direction of the idea of Macs with “boundless” memory; where data’s presence on the machine is fluid, and unnecessary for the the user to worry about.

Apple’s work on search in Photos could open many doors through the use of advanced computer vision and machine learning. Apple Pay on the web imagines a future without worrying about entering credit card information into insecure web pages. Nearly every aspect of Sierra is looking to the future.

Time will tell which of these new directions will pay off. We’ll revisit them next year for macOS 10.13, and see where Apple has continued to take them. While future updates may hold more excitement, macOS Sierra brings improvements without compromise. It is a solid addition to the foundation of macOS, and both the system and its users are better off because of it.

Surprisingly, it’s possible to activate Picture in Picture mode on YouTube. You just have to right click twice in a row, which will cause a second menu to pop up that contains an “Enter Picture-in-Picture” option. ↩︎