Windows hasn’t changed much for end users in the last 25 years, fundamentally at least. From Windows 3.0 to Windows 10, the operating system fit the simple bill as a collection of programs performing various functions and tasks, running in windows, aiding users with a graphical environment and support for precision input devices.

But with Windows 10 Anniversary Update, Microsoft builds upon the transformative element, first introduced in Windows 10, which could herald the most significant OS shift for users since the invention of the GUI, mouse, and keyboard: Cortana.

Cortana represents the future of computing

This is because Cortana is more than just Microsoft’s voice-activated digital assistant. It’s the digital personification of connectivity; the name and voice that bring together the disparate programs, apps, systems, and services that make up modern computing.

Or at least that’s Microsoft’s goal, because it’s not there yet. In fact, even with the new Anniversary Update features bringing it to the forefront, it has a long way to go.

The Future with Cortana

Sticking with pure utility, Cortana can do more. Microsoft extended its reach to additional programs and broadened its capabilities. It’s especially good at creating and scheduling meetings, alerting users to any potential conflicts. Lunch meetings are a focus, with Microsoft claiming it has the capability to work with other Windows apps for restaurant recommendations, takeout, and reservations.

But it’s not that robust just yet. We scheduled dozens of lunch meetings with nary a restaurant suggestion or offer to make a reservation, even after enabling every possible setting and installing every conceivable restaurant app from the Windows Store.

The same is true of Cortana’s contextual awareness. At Build 2023, Cortana wowed attendees by processing the command, Send Chuck the PowerPoint I worked on yesterday.  We were not able to duplicate the results, though Cortana proved adept at offering up the proper presentations, documents, and spreadsheets.

Cortana also does well recognizing words like tomorrow and next . But for all of it to come together to send Chuck the PowerPoint requires the kind of coordination and file management that exists for tech demos but not in real life.

Cortana has some contextual awareness, but still not enough

Many users, including the entire team atNotebookReviewhave a mishmash of contacts, pulled from various accounts and services, complete with duplicate and triplicate entries, and out-of-date information.

The same is true with files. We have them spread across multiple services like OneDrive, Google Drive, and Dropbox, not to mention devices, using office apps from Microsoft, Google, Apple, and others. In Microsoft’s perfect world, we’d keep things neat and orderly with the People app, OneDrive, and official Office. Cortana is just not ready for our messy reality.

The good news is that Microsoft gets this. The Cortana Android app can reroute missed SMS texts and call notifications to the new Windows 10 Action Center, and enable responses through the smartphone, a capability they could have easily limited to Windows Phones. It’s still finicky and too inconsistent to be reliable, but it’s a great start — and a Windows feature we’ve been craving long before Apple devotees had something similar with Continuity.

Cortana has a few new tricks with other apps and services, as well. It pops up on the lock screen for limited commands, and while online shopping in the Edge browser, searching for coupon codes. It also works with Microsoft’s Groove Music Pass, playing songs, artists, and songs via voice. Cortana’s excellent reminders can be supplemented with now. And users can now set, check in on, and cancel timers independent of a dedicated Timer app.

New Inking

Looking through the forest for the trees, Windows 10 Anniversary Update is collection of small features and added controls. Inking is very salient, with the new Windows Ink Workspace, accessible via a new taskbar shortcut. It combines sticky notes, sketchpad, and screen sketch, along with any other pen-supporting apps.

Sticky notes is the highlight. As of this writing, it can recognize dates and words like tomorrow to form quick reminders. Going forward, Microsoft claims it will also recognize locations, phone numbers, and other contextual information.

The sketchpad ruler is another excellent addition, providing a digital straight edge for sketchers. We’d love to see this expanded to other apps, and include other drawing aids like a French curve or protractor.

Sketchpad in Windows 10 Anniversary Update

Microsoft also demoed inking with maps at Build. Users will be able to draw lines to measure distances between two points. But that function has not yet launched.

A Better Edge

Microsoft throws a little love at Edge, finally enabling browser extensions. There are only 13 at launch, including: AdBlock, Adblock Plus, Pin It Button, Translator for Microsoft Edge, Last Pass: Free Password Manager, OneNote Web Clipper, Evernote Web Clipper, Amazon Assistant, Office Online, Save it to Pocket, Reddit Enhancement Suite, Mouse Gestures, and Page Analyzer.

Microsoft Edge browser extensions

Edge is much better at handling Flash, pausing Flash ads and any other superfluous Flash-based content. Users can now pin tabs (finally!), and sites can deliver notifications directly to the desktop Action Center. Microsoft also brought back the swipe-based navigation scheme that debuted in IE for Windows 8.

Microsoft Edge is playing catch up with Google Chrome, especially with the extensions, and there is still little reason for a heavy Chrome user (like many of us here at NBR) to make the switch. But the one thing Edge has on Chrome is performance, namely battery drain. In fact, Microsoft delivers notifications touting Edge’s battery use advantage to heavy Chrome users. And that’s enough for us to keep it up to date and use it from time to time. Edge’s power sipping will come in handy on the next long flight or car ride.

Taskbar and Action Center

Notifications are much improved in the Action Center. Users can set granular priority by app, and a notification cap to prevent things like email messages from overtaking the Action Center. The Action Center and some app taskbar icons now include the number of notifications, and the taskbar Calendar displays daily agenda items. The taskbar also extends to external displays with the clock and calendar on board.

New Windows 10 Action Center

Connect App

Finally, an easy way to share displays! Almost. The new Connect app serves to wirelessly project, connect, extend, and duplicateWindows 10 and Android displays between devices (sorry iOS users, it’s still too locked down for this kind of sharing). It also works with Windows Continuum. Rather than overtaking the entire device with screen sharing, it acts as any other app that can be resized, minimized, maximized, and closed.

Microsoft Connect app

It’s based on Miracast, so that’s a limiting factor, especially when it comes to older devices. On top of that, it’s buggy. In fact, it barely works.

We love the thought of using an old PC as a second screen, and can see Microsoft extending the app for business presentations. Imagine mirroring one display on dozens in a meeting environment. There’s a ton of potential here. But right now it’s purely a 1-to-1 connection, and it’s in pre-alpha levels of functionality.

UI Tweaks

As with any major update, there are many small tweaks and refinements. For Windows 10 Anniversary Update, that includes a new dark theme buried in the settings, and a slightly refined Start Menu.

Start Menu with three rails

The Menu now has three rails, with the new left rail housing settings, accounts, power, and file explorer shortcuts. All apps have been freed from the secondary menu and shortcuts are front and center, underneath recently added apps and most used. Microsoft also included a suggested apps portion that serves as a glorified ad, which can fortunately be disabled.

Other notable tweaks include simple media controls for the minimized Groove Music player, accessible when hovering over the taskbar icon, and the ability to switch audio sources on the fly, also from the taskbar. We love the latter feature, which makes switching from external Bluetooth speakers to the device speakers or Bluetooth headphones a breeze.

Oh, and there are new emojis.

For the Power Users

Much was made of the new Bash shell supportin Windows 10 in the developer community, but for power users, other new features will aid in day-to-day use.

Pinning programs between virtual desktops is an overdue addition, enabling users to keep important programs running and accessible between different work environments. We use it for Slack, but also Slingbox during the 2023 Summer Olympics.

Pinned programs

The DIY set will love the new Activation troubleshooter, which makes activating and reactivating Windows much easier on new or upgraded hardware. It does this by linking your Windows Key to your digital Microsoft account, and not a device.  

Battery Saver is now just Battery, and it allows more granular power management controls. Managed by Windows is the new option for background apps, enabling Windows to pause background apps to conserve power.

Windows Hello, the biometric security standard, is coming to apps, and eventually Edge for website and service login. We weren’t able to test it out on our review copy, but given Windows Hello’s inconsistency, we’ll stick with inputting passwords for now

And More

Skype makes its grand return in app form as Skype Preview, complete with bots. It’s baked into Windows 10 now, so it can receive calls even when not open. Some of the bots have potential at launch, but most are silly trivia games and promotional junk (want to trade messages with Spock? ). We’ll probably hit up Hipmunk, a travel companion that scours the web for flight deals and travel advice, before the next trip, but there’s nothing here that wows us just yet. And we’re still waiting on Skype’s real-time translation feature, which is absent.

Skype Preview with Hipmunk bot

Xbox Play Anywhere has some serious potential, as it enables cross-platform purchases, saves, and multiplayer. In fact, we’ve been waiting on this for years, going back to Xbox Live, Windows Phone 7, and Windows 8. We’ll know more about it when the first wave of games launch next month.

And that’s not all. Every time we power up, we find new features, like Windows Defender’s Periodic Scan that works in conjunction with third-party security software(Windows Defender would take a backseat to third-party software previously), the controversial Wi-Fi Sense feature is gone, the lock screen has a new UI scheme and features media controls, and Windows update gives users more say in when and how Windows applies updates.

Cortana is the Future

As Cortana progresses, it will fundamentally change how we interact with Windows and PC computing. It has a long way to go (there’s a reason Siri was in beta for two-plus years), but the beauty of natural speech recognition is that every failed command is a learning opportunity for Microsoft.   

From Windows 10 Anniversary Update it’s obvious Microsoft is focused on bringing Cortana front and center, making it the primary means to actually use a Windows PC. In the near future, we be dictating and sending a message through Cortana rather than opening the email app and pounding away on the QWERTY, or booking flights on command, with Microsoft’s new bots tying into the effort. This way, Microsoft can divorce computing functions from the hardware.

And it’s not alone. Google is doing the same with its Google Home speaker and its various Android spinoffs. Amazon is pushing Alexa and the Amazon Echo products. Siri is Apple’s answer to Cortana, and Facebook has its army of Messenger bots.

It’s no longer about hardware or platforms vying for market dominance, Microsoft, Google, Apple, Facebook, Amazon and others are battling to serve as the connecting tissue between apps, services, and products. Windows 10 Anniversary Update brings Microsoft a few steps closer to that goal, and more than a few steps ahead of Apple. But it still has a long way to go.