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iOS and iPadOS 14: The MacStories Review

Even with (unsurprisingly) smaller releases, Apple is pushing forward with bold ideas across all platforms.

How do you prepare a major new version of an operating system that now spans two separate platforms, which will be installed on millions of devices within a few hours of its release, amid a global pandemic? If you’re Apple, the answer is fairly straightforward: you mitigate the crisis by focusing on a narrower set of features, perhaps prioritizing bug fixes and stability improvements, but then you just have to do the work.

In my time as an iOS (then iOS and iPadOS) reviewer, I never thought I’d have to evaluate an OS update with the social and political backdrop of iOS 14. Let’s face it: when the COVID-19 outbreak started fundamentally changing our lives earlier this year, at some point many of us – including yours truly – thought that, among more serious and severe repercussions, our tiny corner of the Internet would see no new phones, OS updates, videogame consoles, or other events over the course of 2020. Or that, at the very least, changes in hardware and software would be so minor, they’d barely register in the grand scheme of things as tech companies and their employees were – rightfully so – adjusting to a new, work-from-home, socially distant life. Yet here we are, over a year after the debut of iOS and iPadOS 13, with brand new versions of both operating systems that were announced, as per tradition, at WWDC a few months ago. Remove all surrounding context, and you wouldn’t guess anything has changed from 2019.

Context is, however, key to understanding Apple’s background and goals with iOS and iPadOS 14, in a couple notable ways.

First, I think it’s safe to assume slowing down to reassess the state of the platform and focus on quality-of-life enhancements and performance gains would have worked out in Apple’s favor regardless of the pandemic. In last year’s review, I noted how the first version of iOS 13.0 launching to the public wasn’t “as polished or stable as the first version of iOS 12”; in a somewhat unpredictable twist of events, managing the iOS 13 release narrative only got more challenging for Apple after launch.

Late in the beta cycle last year, the company announced certain iOS 13 features – including automations in Shortcuts and ETA sharing in Maps – would be delayed until iOS 13.1, originally scheduled for September 30th. Following widespread criticism about bugs, various visual glitches, and stability issues in iOS 13.0, Apple moved up the release of iOS 13.1 and iPadOS (which never saw a proper 13.0 public release) by a week. Despite the release of a substantial .1 update, the company still had to ship two additional patches (13.1.1 and 13.1.2) before the end of September. Before the end of 2019, all while the general public was lamenting the poor state of iOS 13’s performance (just Google “iOS 13 buggy”, and you’ll get the idea), Apple went on to ship a total of eight software updates to iOS 13 (compared to iOS 12’s four updates before the end of 2018). The record pace, plus the mysterious removal of features that were originally announced at WWDC ‘19, suggested something had gone awry in the late stages of iOS 13’s development; it wasn’t long before a report covered Apple’s plans to overhaul its software testing methodology for iOS 14 and 2020. The pandemic may have forced Apple to scale back some functionalities and deeper design changes this year, but it’s likely that a decision had been made long before lockdowns and work-from-home orders.

Second, context is necessary because despite the pandemic and rocky rollout of iOS 13 and its many updates, Apple was still able to infuse iOS and iPadOS 14 with fresh, bold ideas that are tracing a path for both platforms to follow over the next few years.

On the surface, iOS 14 will be widely regarded as the update that brought a redesigned Home Screen and a plethora of useful quality-of-life additions to the iPhone. For the first time since the iPhone’s inception, Apple is moving past the grid of icons and letting users freely place data-rich, customizable widgets on the Home Screen – a major course correction that has opened the floodgates for new categories of utilities on the App Store. In addition to the upgraded Home Screen, iOS 14 also offers welcome improvements to long-standing limitations: phone calls can now come in as unobtrusive banners; Messages borrows some of WhatsApp’s best features and now lets you reply to specific messages as well as mention users; Siri doesn’t take over the entire screen anymore. There are hundreds of smaller additions to the system and built-in apps in iOS 14, which suggests Apple spent a long time trying to understand what wasn’t working and what customers were requesting.

iOS and iPadOS 14 aren’t just reactionary updates to criticisms and feature requests though: upon further examination, both OSes reveal underlying threads that will shape the evolution of Apple’s platforms. With compact UI, the company is revisiting a principle introduced in iOS 7 – clarity and content first – with fresh eyes: the UI is receding and becoming more glanceable, but the elements that are left are as inviting to the touch as ever – quite the departure from Jony Ive’s overly minimalistic, typography-based approach. We see this trend everywhere in iOS 14, from phone calls and Siri to widgets, new toolbar menus, and Picture in Picture. Intents, the existing technology behind SiriKit, Shortcuts, and intelligent Siri suggestions, is also at the center of widget personalization. Intents already was one of Apple’s most important frameworks given its ties to Siri and on-device intelligence; iOS 14 proves we haven’t seen all the possible permutations and applications of Intents yet.

Then, of course, there’s iPad. In iPadOS 14, we see the logical continuation of pointer and trackpad support introduced earlier this year in iPadOS 13.4: now that users can control an iPad without ever touching the screen, Apple is advising third-party developers to move away from iPhone-inspired designs with apps that are truly made for iPad…and somewhat reminiscent of their macOS counterparts. We can see the results of this initiative in modernized system apps that take advantage of the iPad’s display with a sidebar, multiple columns, and deeper trackpad integration – new options that every iPad app developer could (and, according to Apple, should) consider going forward. Although some of the iPad’s oft-mentioned ongoing struggles remain unaddressed in iPadOS 14 (see: multitasking and window management), Apple is embracing the iPad’s nature as a modular computer this year, and they feel comfortable leaning into lessons learned with the Mac decades ago.

The context of 2020 is what makes iOS and iPadOS 14 so fascinating and, to a certain extent, fun to review. On one hand, we have two major OS updates that may or may not have been impacted by the global pandemic in their focus on fewer groundbreaking additions and more consistent improvements across built-in apps; on the other, just like any other year, we have a suite of overarching themes and potential implications to dissect.

But for all those users still pausing over that ‘Install’ button, pondering whether updating their most important communication and work-from-home devices is worth it, there’s only one consideration that matters:

Will this go any better than last year?

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    Textastic: The Code Editor for Your iPad and iPhone [Sponsor]

    Textastic is the most complete and versatile code editor available for your iPad and iPhone. The app’s versatility starts with its extensive support of syntax highlighting for more than 80 programming and markup languages. Textastic handles highlighting for HTML, JavaScript, CSS, PHP, C, C++, Swift, Objective-C, Java, LaTeX, Python, Ruby, Perl, Lua, and dozens more.

    Textastic is also a full-featured Markdown text editor that includes a built-in web server and Safari support for previewing your work. The app is compatible with Sublime Text and TextMate syntax definitions too.

    Textastic goes well beyond the features of a classic text editor, though. You can manage remote file transfers with FTP, SFTP, WebDAV, Dropbox, and Google Drive and there’s a terrific, full-featured SSH terminal built right into the app. Because Textastic supports tabs, you can even have multiple files and SSH terminals open simultaneously.

    With robust search and replace that supports regular expressions, keyboard shortcuts that are customizable, and support for Git repositories using Working Copy, it’s the most powerful code editor you’ll find anywhere with a long list of features, including support for the Files app, drag and drop, printing, iCloud Drive, Split View, multiwindowing, context menus, and a whole lot more.

    The app is regularly updated and maintained too. With the release of version 9.3 in June, Textastic gained new keyboard shortcuts for code comments, a setting for automatically inserting a matching closing character for parentheses, square brackets, and curly brackets, code awareness that allows for automatic indentation based on syntax context, an adjustable line height setting, and a setting for displaying the selected line indicator in a document’s gutter. Dark mode has been improved too, allowing users to select a separate code editor theme and keyboard appearance and preview Markdown using a dark color scheme.

    To learn more about Textastic and what it can do for your code editing needs on the iPhone and iPad, visit textasticapp.com, to download a copy today. You’re going to love it.

    Our thanks to Textastic for sponsoring MacStories this week.

    Ulysses 19 Brings iPad Cursor Support, External Folders, Material Sheets, and More

    The latest version of Ulysses, the excellent Markdown editor, is available now. Ulysses 19 offers enhancements in several different areas, from fully optimizing for the new iPadOS cursor, to supporting external folders for the first time, introducing a new ‘material’ designation for sheets, and adding keyword improvements, exportable backups, and even a new font. It’s a strong update, and one that continues to prove Ulysses the best app for my writing needs.

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    Modular Computer: iPad Pro as a Tablet, Laptop, and Desktop Workstation

    My iPad Pro desktop setup.

    My iPad Pro desktop setup.

    When I started my iPad-only journey in 2012, I was stuck in a hospital bed and couldn’t use my Mac. It’s a story I’ve told many times before: I had to figure out a way to get work done without a Mac, and I realized the iPad – despite its limited ecosystem of apps and lackluster OS at the time – granted me the computing freedom I sought. At a time when I couldn’t use a desk or connect to a Wi-Fi network, a tablet I could hold in my hands and use to comunicate with remote colleagues over a cellular connection was all I needed. Over time, however, that state of necessity became a choice: for a few years now, I’ve preferred working on my iPad Pro and iPadOS (née iOS) in lieu of my Mac mini, even when I’m home and have access to my desk and macOS workstation.

    The more I think about it, the more I come to this conclusion: the iPad, unlike other computers running a “traditional” desktop OS, possesses the unique quality of being multiple things at once. Hold an iPad in your hands, and you can use it as a classic tablet; pair it with a keyboard cover, and it takes on a laptop form; place it on a desk and connect it to a variety of external accessories, and you’ve got a desktop workstation revolving around a single slab of glass. This multiplicity of states isn’t an afterthought, nor is it the byproduct of happenstance: it was a deliberate design decision on Apple’s part based on the principle of modularity.

    In looking back at the past decade of iPad and, more specifically, the past two years of the current iPad Pro line, I believe different factors contributed to making the iPad Pro Apple’s first modular computer – a device whose shape and function can optionally be determined by the extra hardware paired with it.

    The original iPad Pro showed how Apple was willing to go beyond the old “just a tablet” connotation with the Apple Pencil and Smart Keyboard. Three years later, the company followed up on the iPad Pro’s original vision with a switch to USB-C which, as a result, opened the iPad to a wider ecosystem of external accessories and potential configurations. At the same time, even without considerable software enhancements by Apple, the creativity of third-party developers allowed iPad apps to embrace external displays and new file management functionalities. And lastly, just a few weeks ago, Apple unveiled iPadOS’ native cursor mode, finally putting an end to the debate about whether the iPad would ever support the desktop PC’s classic input method.

    The intersection of these evolutionary paths is the modern iPad Pro, a device that fills many roles in my professional and personal life. Ever since I purchased the 2018 iPad Pro1, I’ve been regularly optimizing my setup at home and on the go to take advantage of the device’s versatility. I’ve tested dozens of different keyboards, purchased more USB-C hubs than I care to admit, and tried to minimize overhead by designing a system that lets me use the same external display and keyboard with two different computers – the Mac mini and iPad Pro.

    At the end of this fun, eye-opening process, I’ve ended up with a computer that is greater than the sum of its parts. By virtue of its modular nature, I find my custom iPad Pro setup superior to a traditional laptop, and more flexible than a regular desktop workstation.

    So how exactly did I transform the iPad Pro into this new kind of modular computer? Let’s dig in.

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    The Mighty mini: Adapting Apple’s Diminutive Tablet to Work and Play

    Make no mistake, whether it’s a Mac, iPhone, or an iPad, I prefer big screens. I think most people do. A big, bright screen makes reading easier, and a larger canvas for the apps you use is rarely a downside.

    Still, there’s a reason we carry mobile phones when a tablet, laptop, or desktop could accomplish the same tasks: portability. Smaller is often better, even as the compromises start to pile up when you shrink a device.

    Portability is why foldable phones have captured the imaginations of so many people. They promise the portability of a traditional smartphone with a screen that’s closer to a tablet’s.

    Just over one year ago, in March 2019, Apple released two new iPads: a 10.5-inch iPad Air and the first new iPad mini in over three years. The 5th-generation mini was a big surprise, largely because the mini hadn’t been updated in so long, leading many people to write it off as dead.

    Perhaps an even bigger surprise, however, was the mini’s hardware. The design didn’t change, but the 5th-generation mini upgraded the device to an A12 processor, the same chip in the then-current iPhone XR and XS. The update also added a Retina laminated screen with True Tone, P3 color support, and the highest pixel density of any iPad. The mini doesn’t support ProMotion, it only supports the first-generation Apple Pencil, and still relies on Touch ID for security. Still, in terms of raw horsepower, the mini is more similar to the 10.5-inch iPad Air than it is different, allowing it to hold its own in Apple’s iPad lineup despite its diminutive size.

    Table of Contents

    The previous fall, I had ordered a 2018 12.9-inch iPad Pro and fell in love with it for writing and other tasks. As much as I enjoy the iPad Pro’s big display, though, it’s not suited for every task. For example, the size of the iPad Pro makes it awkward for reading in bed. Also, although I love to play games on my iPad Pro with a connected controller, that only works well if the iPad is sitting on a table.

    When the mini was introduced, I immediately wondered whether Apple’s smallest tablet could be the perfect complement to its largest iPad Pro: a powerful but tiny device that could work well where the Pro doesn’t. I also figured the mini could be a great ‘downtime’ device for activities like games, reading, chatting with friends, and watching TV, movies, and other video content. So, I sold some old gear I no longer used and bought a mini with 256GB of storage, so I’d have plenty of space for games and locally-downloaded video.

    The plan was for my new mini to serve almost exclusively as my downtime iPad. What’s happened in practice during the past year is very different than I anticipated originally. My use of the mini has expanded far beyond what I’d expected, despite the compromises that come along with its small size. The iPad Pro remains the device I rely on for most of my needs, but as we approached the iPad’s first decade, the time felt right to consider how far the mini has come and how this unassuming device fits so neatly into the spaces between the other devices I use.

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    Exploring the Most Impactful iPad Apps of the Decade


    John: It’s hard to understate the importance of the iPad’s large screen. Early critics dismissed the device as a big iPhone, but that criticism revealed a fundamental misunderstanding of the product.

    By jumping from the iPhone’s small 3.5-inch display to one that approached 10 inches, the iPad delivered a canvas that allowed Apple and third-party developers to rethink not just the concept of mobile apps, but of apps altogether. The additional screen real estate allowed developers to flatten and spread UIs in a way that made new uses possible. That, in turn, led to richer, deeper experiences for everything from reading a comic book to managing complex projects and automating repetitive tasks, allowing users to interact directly with the software beneath their fingers.

    After years of using the very best apps developers have to offer on the iPad, it was remarkably easy for Federico, Ryan, and I to come up with a list of the iPad apps that have been the most impactful for us during the past decade. There’s a lot of factors at play in arriving at these apps. Some forged a path by adopting the latest Apple technologies in a unique way that set an example for apps that followed. Others are apps that define a category that takes unique advantage of the iPad’s hardware. These are also apps that work on the iPhone or Mac too, but are most at home on the iPad’s unique platform.

    Although there is no single formula for which iPad apps have been the most impactful, one thing each app in this collection shares is a rich, personal experience. These are apps inspired by and reflected in the image of Steve Jobs sitting onstage in a comfortable black leather chair swiping through photos. The iPad and the apps that run on it have come a long way since then, but the intimacy of directly manipulating apps that transform a slab of glass into anything a developer can imagine hasn’t changed, and remains what makes the iPad so special.

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    The iPad at 10: Emerging from the Shadow of the iPhone

    The trouble with looking back over a long period is that time has a way of compressing history. The clarity of hindsight makes it easy to look back at almost anything and be disappointed in some way with how it turned out years later.

    We certainly saw that with the anniversary of the introduction of the iPad. Considered in isolation a decade later, it’s easy to find shortcomings with the iPad. However, the endpoints of the iPad’s timeline don’t tell the full story.

    It’s not that the device is short on ways it could be improved; of course, it isn’t. However, the path of the iPad over the past decade isn’t a straight line from point A to point B. The iPad’s course has been influenced by countless decisions along the way bearing consequences that were good, bad, and sometimes unintended.

    The 10th anniversary of the iPad isn’t a destination, it’s just an arbitrary point from which to take stock of where things have been and consider where they are going. To do that, it’s instructive to look at more than the endpoints of the iPad’s history and consider what has happened in between. Viewed from that perspective, the state of the iPad ten years later, while at times frustrating, also holds reason for optimism. No single product in Apple’s lineup has more room to grow or potential to change the computing landscape than the iPad does today.

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    Textastic: The Code Editor for Your iPad and iPhone [Sponsor]

    Textastic is the most complete and versatile code editor available for your iPad and iPhone. The app’s versatility starts with its extensive support of syntax highlighting for more than 80 programming and markup languages. Textastic handles highlighting for HTML, JavaScript, CSS, PHP, C, C++, Swift, Objective-C, Java, LaTeX, Python, Ruby, Perl, Lua, and dozens more.

    Textastic is also a full-featured Markdown editor that includes a built-in web server and Safari support for previewing your work. The app is compatible with Sublime Text and Textmate syntax definitions too.

    Textastic goes well beyond the features of a classic editor, though. You can manage remote file transfers with FTP, SFTP, WebDAV, Dropbox, and Google Drive and there’s a terrific, full-featured SSH terminal built right into the app. Because Textastic supports tabs, you can even have multiple files and SSH terminals open simultaneously.

    With robust search and replace that supports regular expressions, keyboard shortcuts that are customizable, and support for Git repositories using Working Copy, it’s the most powerful code editor you’ll find anywhere with a long list of features, including support for the Files app, drag and drop, printing, iCloud Drive, Split View, and a whole lot more.

    The app is regularly updated and maintained too. With the recent release of version 9, the app supports dark mode, multiwindowing, and context menus. Context menus are perfect for accessing a wide range of editing functions, managing multiple windows, and quickly grabbing a document’s file path.

    To learn more about Textastic and what it can do for your code editing needs on the iPhone and iPad, visit textasticapp.com, then download a copy today. You’re going to love it.

    Our thanks to Textastic for sponsoring MacStories this week.

    My Must-Have Apps, 2019 Edition

    My Home screens.

    My Home screens.

    Every year in late October, I start putting together a rough list of candidates for my annual ‘Must-Have Apps’ story, which I’ve historically published in late December, right before the holiday break. As you can tell by the date on this article, the 2019 edition of this story is different: not only did I spend the last months of the year testing a variety of new apps and betas, but I also kept tweaking my Home screen to accomodate MusicBot and new Home screen shortcuts. As a result, it took me a bit longer to finalize the 2019 collection of my must-have apps; in the process, however, I’ve come up with a slightly updated format that I believe will scale better over the next few years.

    In terms of app usage, 2019 was a year of stabilization for me. Having settled on a specific writing workflow revolving around iA Writer and Working Copy, and having figured out a solution to record podcasts from my iPad Pro, I spent the year fine-tuning my usage of those apps, refining my file management habits thanks to iPadOS’ improved Files app, and cutting down on the number of apps I kept tucked away in folders on my iPhone and iPad.

    Two themes emerged over the second half of 2019, though. First, thanks to various improvements in iOS and iPadOS 13, I increased my reliance on “first-party” Apple apps: I embraced the new Reminders app and its exclusive features, stopped using third-party note-taking apps and moved everything to Notes, and switched back to Apple Mail as my default email client. I’ve written about the idea of comfort in the Apple ecosystem before, and I’ve seen that concept work its way into my app preferences more and more over the course of 2019.

    The second theme, unsurprisingly, is my adoption of a hybrid Home screen that combines apps and shortcuts powered by our custom MacStories Shortcuts Icons. Following changes to running shortcuts from the Home screen in iOS 13, I realized how much I was going to benefit from the ability to execute commands with the tap of an icon, so I decided to mix and match apps and shortcuts on my Home screens to maximize efficiency. Thanks to the different flavors of MacStories Shortcuts Icons (we just launched a Color set), I’ve been able to assemble a truly personalized Home screen layout that puts the best of both worlds – my favorite apps and custom shortcuts – right at my fingertips.

    For this reason, starting this year you’ll find a new Home Screens section at the beginning of this roundup that covers the first tier of my must-have apps – the “ultimate favorites” I tend to keep on the Home screens of both devices. Because I like to keep my iPhone and iPad Home screens consistent, it made sense to start grouping these apps together in their own special section. These are the apps I use most on a daily basis; I’m pretty sure you’ll find at least a couple surprises this year.

    This entire story features a collection of the 50 apps I consider my must-haves on the iPhone and iPad, organized in seven categories; whenever possible, I included links to original reviews and past coverage on MacStories. As for the traditional list of awards for best new app and best app update: those are now part of our annual MacStories Selects awards, which we published last December and you can find here.

    Let’s dig in.

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