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iOS 16: The MacStories Review

Customization is back, and Apple’s having fun again.

When is the last time your iPhone truly surprised you?

The answer to this question is a fascinating Rorschach test that can say a lot about a person’s relationship with Apple’s mobile platform. Some might say it was over a decade ago, when they feasted their eyes upon the Retina display for the first time in 2010. Some might say it happened when the iPhones got bigger – and sales skyrocketed – with the iPhone 6 lineup in 2014. Others might argue that it happened with Face ID on the iPhone X, or the first time they tried Portrait or Night mode, or perhaps when they first took an ultra-wide shot.

My point is: if you ask someone about the last time an iPhone truly surprised them, chances are they’ll reply with a hardware feature. That’s not a shocker: Apple prides itself upon the tight integration they’ve been able to achieve between the iPhone’s hardware and iOS; they’ve successfully managed to turn their design philosophy into a selling point of their entire ecosystem.

People buy iPhones because they know they’re going to work well for a long time, and, usually, because the model they’re getting has a cool new gimmick they want to try. For this reason, it’s not absurd to postulate that, by and large, the iPhone’s software serves to enable hardware sales and subscriptions. I do not mean this pejoratively: I like Apple’s approach, otherwise I wouldn’t be writing annual reviews about their operating systems. But I also recognize that on the iPhone (the situation is the exact opposite on iPad) the software now largely takes the backseat compared to hardware and services.

Which is why whenever the iPhone’s software truly surprises me, I get excited.

Software-related surprises are more rarefied on iOS these days, but the kind of people who are reading this story can point to a few examples in our recent history. Apple buying Workflow, turning it into a system app, and outright claiming that Shortcuts is the future of automation was a surprise. The extent to which Apple integrated dark mode in iOS 13 was a surprise.1 The arrival of two iPad features – Picture in Picture and inter-app drag and drop – on iPhone felt like a surprise. But, of course, no modern feature comes close to the surprise that we all witnessed with iOS 14 two years ago: a renewed focus on user personalization with custom Home Screen widgets and the ability to create multiple Home Screens.2

That’s why, following last year’s welcome (if perhaps a tad uninspired) quality-of-life update that was iOS 15, I’m excited about a new version of iOS again.

iOS 16, launching today for a variety of iPhone models dating back to the iPhone 8, marks Apple’s triumphant return to user personalization, with a twist: while in 2020 customization might have felt like a happy consequence of Apple’s engineering, this time the company has intentionally marketed iOS 16 as an update that will make an iPhone feel truly your own. As we explored in June and July, the first thing you see on your iPhone – the Lock Screen – is fundamentally changing in iOS 16. With the ability to create multiple Lock Screens, choose from a diverse collection of wallpaper sets, and customize each one with widgets, you’ll now have endless possibilities for the screen you always see when you pick up your iPhone.

Sure, there’s an argument to be made for Lock Screen widgets also being developed in service of new hardware, but I don’t think that takes away from the breadth of this feature and how Apple created a whole narrative around wallpapers, widgets, photos, and Focus modes this year. As you’ll see, the customizable Lock Screen will be the main character of this review: I’ve had a lot of fun exploring different permutations of my Lock Screen this summer, and I’ve been able to test dozens of widgets from third-party developers, which I’ll also showcase in this story.

In keeping with my theory that modern iOS updates always need to have a little bit of something for everyone, there’s a ton of other (some bigger, some smaller) features I’ll be covering in this review.3 Messages, one of my most used apps on iPhone, has received a substantial update with the ability to edit and un-send messages, making it, in some ways, even superior to WhatsApp for me now. Mail – of all apps – has gotten a major upgrade with modern features such as scheduled send and, almost unbelievably, a revamped search that actually works. Reminders has officially turned into a serious task manager with even more filters for smart lists and the ability to create and share templates with others.

The new Lock Screen takes center stage this year and everything else pales in comparison to the massive update it received, but, overall, I find iOS 16 a more fun and useful update than iOS 15.

So, as with every September: let’s dive in.

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  1. Then again, wasn't that in service of OLED displays? ↩︎
  2. Perhaps the iPhone 14 Pro's Dynamic Island will be another major surprise for iPhone users. Fascinatingly, it's going to be a unique blend of hardware and software that shows how Apple has been playing the long game with their design strategy for the past few years, which is now paying off. However, the iPhone 14 Pro is not out yet and I haven't tested the Dynamic Island, so that's beyond the scope of this review. ↩︎
  3. That's in addition to the apps and features we've already covered in our annual OS Summer Series on MacStories. ↩︎

The 2022 MacStories OS Preview Series: Everything New Coming to Apple Mail

Email isn’t going anywhere anytime soon despite its flaws. Tools like Slack have replaced the lion’s share of internal communications at many companies, and a long list of messaging apps have chipped away at conversations among individuals. Still, email has proven resilient.

One of email’s many problems is how hard it can be to manage the volume of messages so many of us receive. Over the years, developers have come up with innovative tools layered on top of the core email protocols to improve the experience. However, few of them are with us anymore. Remember Sparrow? How about Mailbox or Acompli? Notice a trend? There are still some bright spots, like Mimestream on the Mac and Spark, but with so few survivors, having a strong choice from Apple has never been more important.

That’s why the situation with Apple’s Mail app has been so distressing in recent years. Mail sat, barely touched on any platform for what seemed like forever. However, this fall, across iOS, iPadOS, and macOS, Apple is finally bringing many of the features pioneered by others to its own Mail app. You won’t find every cutting-edge modern email feature in Mail. Message collaboration and back channel chat about email messages among team members, which Spark and other apps offer, is a good example of a feature Apple has left to others. However, I expect most individuals and teams that aren’t looking to use email as though it were Slack will like what they see in Mail, so let’s dig into the details.

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Shortcuts in iOS 16: The Potential of App Shortcuts for Everyone

App Shortcuts in iOS 16.

App Shortcuts in iOS 16.

A note from Federico: This year, I’ve decided to try some new things for my annual iOS 16 review. Some you’ll see on Monday. One of them is previewing small excerpts from the review in the OS Preview series on MacStories and MacStories Weekly for Club MacStories. Today, I’m posting a preview of a section of the Shortcuts chapter here, and a section of the Everything Else chapter in MacStories Weekly. I hope you enjoy these. I’ll see you for the full story – and more reveals – on Monday.

In iOS 16, the Shortcuts app hasn’t undergone a major redesign or technical rewrite; instead, Apple’s efforts have focused on adding more actions for system apps, extending the developer API, bringing more stability, and making Shortcuts more approachable for new users.

The last point is both important and likely the reason why some Shortcuts power users will be disappointed by this year’s update. There isn’t a lot for them in this new version of the app: as we’ll see in my iPadOS review, there’s no integration with Files quick actions, no support for Stage Manager actions, and no system-wide hotkeys still. If you’re an advanced Shortcuts user and were wishing for more system-level enhancements in addition to stability this year: I hear you, but we’ll talk about this later on.

What we do have in iOS 16 is a fascinating new feature to get newcomers started with the Shortcuts app, a grab bag of useful new actions for Apple apps, and some solid developer-related enhancements that will make third-party actions much better than before. Let’s take a look.

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Hands On: iCloud Shared Photo Library and Family Checklist

iCloud Shared Photo Library

Over the years, I’ve shared family photos with my wife Jennifer in three ways: iMessage, AirDrop, and Shared Albums. However, of those, iMessage won hands down, not because it’s the best way to share photos, but because Messages is an app we already use every day to communicate. Plus, sharing photos with Messages is easy whether you’re already in the app and using the Photos iMessage app or in the Photos app itself and using the share sheet. From conversations with friends and family, I know I’m not alone in my scattershot approach to sharing photos with my family.

It’s into that chaotic, ad hoc mess and all of its variations that users have improvised over the years that Apple is stepping in with iCloud Shared Photo Library, its marquee new Photos feature for iOS and iPadOS 16 and macOS Ventura. And you know what? It just works.

The feature lets anyone with an iCloud photo library share part or all of their photo library with up to five other people. Once activated, a new library is created that sits alongside your existing one and counts against the iCloud storage of the person who created it.

One critical limitation of iCloud Shared Photo Library is that you can only be a member of one shared library, a restriction that is designed to limit the library to your immediate household. That means I could share photos with my wife and kids because there are fewer than six of us, but I couldn’t set up another library with my siblings or parents for our extended families. Nor could I invite one of my extended family members to use the extra slot I’ve got in my family library unless they were willing to forego being part of any shared library their own family created.

Unwinding a shared library.

Unwinding a shared library.

So, what do you do if you’re in a shared library and want to join a different one? There’s a button in the Photos section of Settings to leave a library, so you can do so with one tap, saving all of the photos in the shared library to your personal library or keeping just those you originally contributed to the shared pool. Deleting libraries is possible too, but only by the person who created them, who is given the choice of keeping all images or just the ones they contributed when they do so.

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Everything New Coming to the Home App in iOS 16 and macOS Ventura

I’ve spent a lot of time in the Home app since moving to North Carolina. I moved right after WWDC, so I’ve disassembled, reassembled, and reconfigured my home automation setup, all in the midst of testing the latest iOS, iPadOS, macOS, and watchOS betas. What I’ve learned is that the Home app’s new design is much better for navigating a large collection of smart devices than before, but the app’s changes don’t go far enough. The app’s automation options are still too rudimentary, which limits what you can accomplish with them. Still, the update is an important one worth exploring because it promises to relieve a lot of the past frustration with the Home app.

One question that’s fair to ask about Home’s redesign is: Why now? The app’s big, chunky square tiles have been a feature of the app since the start and criticized just as long. The issues that I suspect have spurred the change are two-fold. First, the square tiles of the app’s previous design were too uniform, making it hard to distinguish one device from another. Second, they wasted space. That was less of a concern on a Mac or bigger iPad, but no matter which iPhone you used, Home could never display more than a handful of devices. Both issues have been problematic for a while, but with the Matter standard poised to bring more devices into the Home app, the issues were bound to get even worse without a redesign.

Say goodbye to Home's sea of square tiles.

Say goodbye to Home’s sea of square tiles.

Since Home was first released, Apple has tweaked the iconography available in Home and added a row of status buttons along the top of the app, but the big space-wasting tiles endured. That led me to control my HomeKit devices with Siri most of the time. That’s not a bad way to control devices, but it’s not as reliable as tapping a button. Plus, the app is just more convenient than Siri in many situations, like when I’m already using my iPhone for something else or when it’s early in the morning, and my family is still asleep. That’s why I was so glad to see Apple rethink how Home uses valuable screen space and the way devices are organized.

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The 2022 MacStories OS Preview Series: Maps and CarPlay

I recently moved from Illinois to North Carolina, and I don’t know the area at all. As a result, I’ve been using Maps and CarPlay a lot since I got here. The new features coming this fall to each aren’t as extensive as they’ve been in past years, but there are several small changes that represent the kind of incremental, ‘quality of life’ improvements that I expect users will appreciate.

Maps

Because so much of Apple Maps relies on methodically mapping the world bit by bit, many users are stuck waiting for Maps’ underlying data to catch up with the app’s features. The more detailed maps and 3D models of landmarks introduced last year are good examples. Both came with asterisks because they were only available in certain cities or countries at launch.

This year is a little different. Apple announced new countries and cities where you’ll find the company’s more detailed maps, 3D landmarks, and other changes, but this year, multi-stop routes and tweaks to Maps’ routing UI will be available to everyone at the same time. It’s a nice mix of brand-new features and incremental improvements that includes something for everyone.

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Generating Markdown Links to Mail Messages with Shortcuts and AppleScript

One of the system app updates we covered on AppStories this week that I’m most excited about is Mail. The app will finally introduce several advanced features this fall, including:

  • Undo send, allowing you to recall a message for 10 seconds after sending a message
  • Message scheduling with suggested and fully-customizable future delivery times and dates
  • Follow Up, which surfaces requests you’ve made in messages for which you haven’t received a response
  • Remind Me, a snooze-like feature for scheduling messages to reappear in your inbox later
  • Missing recipient and attachment alerts
  • Improved search

For the first time in quite a while, that list makes Mail a much more attractive alternative to third-party apps. Mail won’t match every feature offered by third parties, but my needs for advanced email client features are fairly modest, which I expect puts me squarely in the demographic that Apple is targeting.

Mimestream offers Gmail's excellent search and other features in a native Mac package.

Mimestream offers Gmail’s excellent search and other features in a native Mac package.

Until recently, my email use was split between Mimestream, which is only available on the Mac, and Spark on iOS and iPadOS. The split wasn’t ideal, but because I handle most of my email on my Mac, I tolerated it.

For the past several weeks, I’ve been using Mail exclusively on all of my devices, which has been a refreshing change of pace. Still, it’s not perfect. Of the features I use most in third-party mail clients, the single biggest shortcoming of Mail is its clunky implementation of deep linking.

I drop links to email messages in my notes and tasks all the time as a way to quickly access important contextual information. Mimestream offers Gmail URLs, and Spark can create its own app-specific and web URLs right within those apps’ UIs.

I like the way drag and drop on the iPhone and iPad links a message to its subject, but having to use drag and drop is clunky.

I like the way drag and drop on the iPhone and iPad links a message to its subject, but having to use drag and drop is clunky.

In contrast, on iOS and iPadOS, you can only link to a Mail message by dragging it out of Mail into another app’s text field. I’ll take it, but I’d prefer if I could quickly generate a link from the share sheet or with Shortcuts instead. The situation on the Mac isn’t much better, requiring users to resort to AppleScript to construct a URL that links back to a Mail message.

With weeks of Ventura testing ahead of me, I decided to see what I could do to improve the situation. The result isn’t perfect: I still have no choice on iOS and iPadOS but to drag and drop messages. However, I’ve improved the experience on the Mac using a combination of AppleScript and a shortcut that I trigger using Raycast to link the subject of a Mail message to its URL. For added context, my shortcut adds the sender’s name too.

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Ventura Adds Shortcuts to Its Share Menu

When Shortcuts debuted on the Mac in Monterey, Apple added more ways to run an automation than anyone expected, but there was one big omission. Shortcuts wasn’t included in Monterey’s share menu. That was a big disappointment for anyone (like me) who has built a lot of shortcuts that rely on the share sheet on iOS and iPadOS. That’s why I’m happy to report that this fall, when Ventura is released, Shortcuts users will, at last, be able to trigger their shortcuts from the Mac’s Share menu.

Enabling Shortcuts's share extension in System Settings.

Enabling Shortcuts’s share extension in System Settings.

Shortcuts was toggled off by default in Systems settings on my Mac, so you may not see it if you go directly to the Share menu. To enable it, open System Settings and go to the Extensions section of the Privacy & Security section, where you’ll find it under Sharing. Once toggled on, you’ll be able to select it like any other Share menu item, which will display a list of shortcuts that accept the input that the app you’re using offers.

Running a Shortcut from the share menu in Safari.

Running a Shortcut from the share menu in Safari.

My testing is ongoing, but despite some bugs, the new Shortcuts share item works well across a variety of system and third-party apps. For example, Safari can pass the active webpage, its URL, and a PDF to Shortcuts, where I’ve used the input with actions like Get Current Web Page from Safari, Get Details of Safari Web Page, and Get Contents of Web Page.

Safari’s inputs also work with File actions like Save File, which can be used to create nicely-formatted PDFs of webpages. However, due to what appears to be a bug in Shortcuts, PDFs can only be saved if the URL is also passed as input to the Save File action, resulting in the creation of a PDF and two HTML files of the webpage contents. Another limit of Safari’s Share menu support is that it currently doesn’t work with text selections.

A PDF of a MacStories article created using Shortcuts via the Share menu.

A PDF of a MacStories article created using Shortcuts via the Share menu.

Safari is where I expect to use Shortcuts’ Share menu the most, but it works with other apps too. So far, I’ve used Shortcuts from the Share menu to:

  • Convert a PNG image to JPEG
  • Open a file from Finder
  • Add a PDF to Keep It for Mac
  • Send a PNG from Pixelmator Pro to Keep It for Mac
  • Add Mac App Store URLs to the Trello board we use to organize our Club MacStories newsletters

There are other ways to accomplish any of these things without a share extension, but the Share menu lets you trigger your shortcuts from the context in which you’re working, which I prefer.

The addition of Share menu support is promising, but it still needs work. In addition to the Safari limitations and bugs I mentioned above, it’s worth noting that if a shortcut fails from the Share menu, the app becomes unresponsive and needs to be quit and restarted before it will work again. Also, Shortcuts’ picker window opens behind the app you’re using, so if your app window is in the center of the screen, Shortcuts’ picker might be hidden. Interaction with the app from which you trigger a shortcut is blocked while your shortcut is running too.

The Share menu, which has undergone a redesign in Ventura, removes a couple of features that would be useful with Shortcuts that I hope are added back. First, it’s no longer possible to reorder share extensions in System Settings. I’d like to move Shortcuts to the top of my list, but I can’t. Second, because the Share menu is now an independent floating pallette instead of a submenu of File → Share, individual share extensions can no longer be assigned a keyboard shortcut in System Settings.

Notwithstanding some rough edges, though, it’s good to see Shortcuts come to the Share menu. I’ve found ways around its omission from Monterey, but none have ever seemed as natural as clicking the share button in an app’s toolbar. Hopefully, by the time it’s released in the fall, Shortcuts’ share extension will do everything on the Mac that it can do on the iPhone and iPad.

watchOS 9: The MacStories Preview

After watching this year’s WWDC keynote in June, my initial impression of the watchOS 9 announcement was that Apple had prepared one of the largest Apple Watch updates in years. While writing my watchOS 9 overview later that day though, it felt like the scope of the changes were less than I originally thought. I needed some hands-on time with the update to know for sure.

I’ve had bad luck installing early watchOS betas in the past, so I’ve been waiting for the public beta to arrive before loading it onto my daily-driver Apple Watch. That said, I installed the developer beta right away onto an extra Apple Watch Series 4 that I’ve kept around, and have been using it as much as possible throughout the past month. I’ve ascertained a good feel for this year’s update, and can confirm that we’re looking at another mild-mannered year for the Apple Watch.

I don’t mean this as an insult at all. Rather, it’s another year of the relentless incremental refinement that Apple has long been known for, but which the company has practically turned into a science for watchOS. The formula looks something like this:

  • A handful of improvements to the Workout app
  • One or two new features targeted at health
  • A handful of new watch faces
  • One or two brand-new first-party apps
  • One or two redesigned first-party apps
  • A system-level feature or improvement

This year’s changes to the Workout app may be more significant than usual, but otherwise watchOS 9 fits this formula quite snugly. While it may not make for the most glamorous year-over-year updates, the strategy has cemented the Apple Watch as the most popular smartwatch in the world — by far. It’s no surprise that Apple sees no need to alter it.

While the formula may have stayed the same, there are still plenty of specifics to dig into. Let’s start with Workout, the app whose changes single-handedly led me to believe that we were getting a bigger-than-usual watchOS update this year.

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