Windows 10 May 2019 Update review: Sandbox and a better Windows Update improve your PC

Microsoft's latest 19H1 feature update isn't as aspirational as Windows 10 once was. And that's OK.

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Tracking your web browsing has been historically limited to Microsoft Edge. Now Timeline tracks Chrome as well, with a Chrome extension you’ll have to download from the Chrome Web Store. You’ll still need to dig to find Timeline’s history of Chrome sites, by clicking the Timeline icon to the right of the Cortana icon on the Taskbar, and then clicking the small “See all XX activities” to the right of the “Earlier Today” header. (Timeline doesn’t track sites you’ve viewed in Incognito Mode.)

Microsoft Windows 10 April 2019 Update timeline for chrome screen Mark Hachman / IDG

Once you do, sites you visit in Chrome (represented by “Web Activities”) will appear. 

We considered adding this to our list of “hidden features” within the May 2019 Update. But this really closes the book on Timeline, a major component of earlier feature updates and much more of an afterthought in the current release.

A revamped Light Theme

We initially left out the updated light theme from our review, if only because a light theme had already been part of Windows, along with the more popular dark theme. But the reworked light theme (Settings > Personalization > Colors) now adjusts the system colors to more consistently lighten them up.

windows 10 may 2019 update light theme Microsoft

The new Windows 10 May 2019 Update light theme.

App updates hide within Windows

App updates used to be part and parcel of new Windows 10 feature updates, as they were more dependent on the services within them. Though app development now largely proceeds independently of Microsoft’s Windows roadmap, it’s still worth looking at how key Windows apps have evolved during the May 2019 Update development period.

Microsoft warned early on that some of what it calls “inbox” apps—the simplified versions of Office apps, such as Mail and Calendar, as well as Photos—had become even more simplified for this release. Fortunately, my beloved Photos app added back its “magic wand” photo-fixing tool that it warned it might remove.

Other changes include:

A redesigned Office app: Microsoft’s “new” Office app didn’t show up on my Insider machine, though it’s really not that much different than the existing Office app. Both apps offer the opportunity to manage installs, select from among Office apps, and more. The new feature appears to be “recommended” documents, as well as a tab to “discover” documents, perhaps tied to Delve. Microsoft wants to facilitate sharing communal documents, and the new app seems designed to do that.

Sticky Notes: I don’t personally use Sticky Notes often, preferring other apps instead. With the Windows 10 May 2019 Update, Microsoft is consolidating Sticky Notes both in the cloud (at https://www.onenote.com/stickynotes) as well as in a column of notes on your PC, which also feature a new dark mode. I don’t like the inability to rearrange the notes. But what Microsoft calls “insights,” such as the app’s ability to recognize a “remind me” note as an actual reminder, remains one of its most potent features. 

Windows 10 April 2019 Update sticky notes large Mark Hachman / IDG

Mail and Calendar: Previously, Mail and Calendar’s dark mode extended only to your inbox, shifting back to a blinding “light mode” when composing a new email. That’s been fixed. But there’s also an option to view emails in light or dark mode via a new “sun/moon” icon that appears in the header bar of the compose pane.

Microsoft Windows 10 April 2019 Update mail dark mode edit Mark Hachman / IDG

Dark Mode extends further into Mail and Calendar, and a new icon has been added to toggle individual items back and forth.

Snip & Sketch: The Windows 10 Snipping Tool has a warm place in my heart, but Snip & Sketch will eventually replace it. I’m liking it more; the interface looks more like a Windows Ink app than anything else, but the functionality is largely duplicated. New this time around is the ability to add a border to your snap of varying thickness and color, to visually delineate a screenshot with a white background. Printing is simpler, too. Both are hidden in the ellipsis menu in the upper right-hand corner.

Your Phone: Because Your Phone is part of Windows 10, but not intrinsically tied to it, it’s possible that you’ll see the ”screen mirroring” feature for Android devices that debuted late in the Insider process. Essentially, Your Phone provides an easy way to transfer photos back and forth between your phone and PC, while mirroring” allows you to see what it would display if you had it in front of you. A “mirrored” phone can’t be seen outside of Bluetooth range, though, which mitigates its appeal somewhat. You’ll also need a supported phone (a Samsung Galaxy or recent OnePlus phone) as well as a PC with Bluetooth Low Energy capabilities, like a Surface Go. It’s a weird, limiting intersection of hardware, all to save a few seconds pulling out your phone.

Windows 10 Your Phone phone mirroring Microsoft

Lightning round!

Though we’ve highlighted some of the top features within the Windows 10 May 2018 Update above, many more lie within.  What we’ve listed below are some of what we’d call the incremental updates: worth mentioning, but just as nominal improvements.

ethernet settings migrate to Settings: Over time, Microsoft has moved more and more functionality away from the legacy Control Panel and into the Settings menu. This trend continues with the ethernet settings.

More apps can be uninstalled: Hate a bunch of legacy or irrelevant apps clogging up your Start menu? Now you can uninstall all of these: 3D Viewer (previously called Mixed Reality Viewer), Calculator, Calendar, Groove Music, Mail, Movies & TV, Paint 3D, Snip & Sketch, Sticky Notes, and Voice Recorder.

Right-click to unpin a Start tile: This is self-explanatory.

”Fix scaling for apps” by default: If you’ve ever connected to an external monitor, you may have received a cryptic message about fixing apps that are blurry (which, to me, never are). Microsoft now just solves any issues it finds, automatically.

Drag-and-drop Fonts: If you want to add fonts to Windows 10 without downloading them directly, there’s an easy way to do it: take the font file and simply drag it to a landing area within the Settings > Fonts folder. 

Microsoft Windows 10 April 2019 Update fonts Mark Hachman / IDG

There’s now a “landing strip” to deposit new Windows fonts upon.

Security keys can be set up inside Settings: With more of a push to add security keys (like Yubikeys) as additional authentications to WebAuthn, Windows has now made it convenient to add a security key, alongside a fingerprint or facial recognition. In fact, the sign-in options in general are simply better organized.

Clipboard history gets compact: Windows Insiders inexplicably voted the more compact Clipboard history their favorite feature. If the tighter organization of content you’ve clipped (CTRL+X) wows you, you’ll love this. 

Windows 10 May Update clipboard history Microsoft

Default sorting within Downloads: If you’re like me, your Downloads (and Pictures) folders go on for miles, often making it difficult to find anything. Downloads now separates downloads by day, highlighting the most recent additions. Interestingly, a previously available option to make dates “friendly” (like Dec. 25, 2019 versus 12/25/2019) isn’t available anymore.

Windows 10 April 2019 Update downloads Mark Hachman / IDG

Windows 10 applies a new chronological hierarchy to files downloaded within the Apri 2019 Update.

Revamped Protection History: Within Protection History (Settings>Windows Security>Virus and Threat Protection>Protection History), Microsoft has revamped the layout to show you any actions that Windows took to protect your PC. Hopefully there’s nothing here—that’s good! But here’s what Microsoft could show you in case there was an attack. 

Conclusion: A light touch 

We entered into this review with measured expectations, but we were pleasantly surprised at how the new update genuinely pushes the PC ahead. True, we have mixed feelings about the separation of Search and Cortana, and the interaction between the Search app and the more traditional File Explorer. Users will undoubtedly muddle through, though. Features like Windows Update show Microsoft’s finally taking some of its criticisms to heart. And hey, kaomoji!

We’re assigning the Windows 10 May 2019 Update an average score for a middling release. But given the windmills Microsoft has tilted at in the past (mixed reality, for example) and the horrendous bugs that overshadowed the last release, a ho-hum feature update isn’t the worst thing in the world. Maybe Microsoft’s developers are working instead on something new, such as the rumored Windows Lite? No matter. Spring is here: Install the Windows 10 May 2019 Update, take a tour of what’s improved, and move on.

Updated on June 3 to add more details about the new light theme.

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At a Glance
  • Pros

    • Windows Sandbox offers a safe space for new apps, sites
    • Most additions improve existing features


    • Minor release in terms of ambition
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