The WWDC hangover and Siri AI blindspots


Apple’s WWDC went about as expected for 2026. While it’s a tiny bit disappointing, Siri AI turned out to be worth the wait, but with some painful app-based gaps.

WWDC 2026 was on Monday, and it was expected to be a bit of a slow one this time around. As predicted by the rumor mill and countless reports in the weeks ahead, it certainly wasn’t an event that shouted about many new features.

Actually, that’s not quite true. Apple did harp on about one big thing, and that was its whole artificial intelligence push.

Sorry. Apple Intelligence and Siri AI.

Before the event, we knew full well that the main beats would basically be Siri and AI stuff, and a bit of periphery. I even asked for there to be something that wasn’t AI to talk about.

Admittedly, Apple did bring up other things that weren’t AI. Except they were not things I could excitedly tell my mother about when explaining the significance of Apple’s launches.

Making things more reliable and responsive? That’s nice, but that’s also what we expect from updates throughout the year anyway.

There was more talk about parental controls and Screen Time updates. This again is great for parents, as now little Timmy can be protected from blood and gore as well as unsolicited nudes.

But neither are things that can be enthused about to friends or people curious about what happened. “Hey, you’ll like how you’ll see confirmation codes on your iPhone screen when you phone a business number” is neat, but not sexy enough to enthuse about.

Really, the only subject worth discussing is the whole AI thing.

Shockingly more intelligent

Apple went into a whole spiel about its artificial intelligence work, complete with handy circle-based graphics explaining the whole ecosystem. The whole thing of using Apple Foundation Models, a “System Orchestrator” connecting stuff together, and the “Systemwide Experiences” with Siri and Apps.

All very nice and showing in a public-friendly way how everything is interconnected and works as a giant whole, without explaining how. For Joe Public, that’s explanation enough.

Circular Apple AI diagram with concentric layers labeled personal context, world knowledge, actions, apps, onscreen awareness, system orchestrator, systemwide experiences, and inner icons for voice, text, image, and user.

An explanatory circle-in-circle explanation of Apple’s AI strategy. At least, it looks explanatory…

The main thing is that Apple’s two-year-late Siri upgrade has finally turned up. It’s late, but surprisingly, it wasn’t disappointing.

What Apple promoted heavily in 2024, the entire contextual-awareness thing, actually works properly. After reaching the end of the waitlist to use Siri AI, as well as the lengthy indexing process, I was able to ask some questions that could easily be troublesome for Old Siri.

The first one was simple. “Where was I born?”

Cue Siri coming up with the correct response of my hometown. What was unexpected was that the detail was picked up because I had a photo stored in iCloud of my passport for identity validation purposes.

Being greeted by the mugshot-like images of my passport and personal information as evidence of where it got the answer from was a bit of a shock.

A second query asking when I last went on vacation was similarly fast. This time, it used a combination of photographs and messages with my partner.

It understood we travelled to Rome in early April 2025, how long we were there for, and that we visited places like the Colosseum and the Roman Forum. Again, providing links to sources for context.

This is quite impressive, as is using the camera to photograph far-away slides in a presentation and asking Siri to summarize it all. The lengthy tiny print became something much easier to digest for my at-the-time tired brain and eyes.

Sure, we wanted it two years ago after Apple first demonstrated the idea. The two-year delay was made worse by seeing other AI firms developing quickly and leaving Siri in their dust.

That said, it was certainly worth the wait.

This is all something that you can enjoy in the fall if you’re not installing the developer betas. Unless you wait for the public betas, or don’t care about any risks to your data.

Except if you’re in the EU. That’s still a mess that Apple needs to clean up.

Massive blind spots

That said, there were some gaps in its capability. For example, it couldn’t generate a list of recent messages in Slack, nor could it work out what my mother last said in Facebook Messenger.

While my AppleInsider email is handled in the Mail app and could be accessed by Siri, my personal email in Gmail could not.

As impressive as Siri AI is, private third-party data sources are probably going to be the stumbling block. Unless apps like Gmail provide access to the data troves in some way, they will be areas that Siri won’t be able to use to help the user.

These data blind spots may be opened up by Google and other sources in the future. But there’s also the temptation to keep them locked off from Siri completely, if only to make their own AI services provide the same functionality.

Google Gemini already has the capability of accessing your Gmail email if you have a supported AI plan. There’s no incentive for Google to let Siri AI do the same and miss out on those consumer subscriptions.

Colorful Apple Intelligence promotional graphic showcasing Siri AI features, including writing assistance, visual intelligence, expressive voices, intelligent photo editing, notification summaries, and app integrations on a dark futuristic background

The only bento box that mattered in WWDC 2026.

Money is always a factor in business decisions, and the massive potential of Siri could influence other big tech rivals not to play ball with Apple’s vision.

I may not be able to access communications from my personal email, but at least Siri can tell me what the lowest-calorie but highest-protein option available at my local KFC is for a post-gym workout.

That would be the grilled chicken salad. It was OK.

Last week’s Sunday Reboot discussed the inevitable Intel hardware and software support changes arriving this fall.



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macOS has a built-in screenshot tool that gets the basics right. You can take a screenshot, record your screen, and even annotate your captures. But the moment you want something more, like scrolling capture, advanced annotation tools, or a quick way to share your screenshots via a link, it starts to fall apart.

That’s where CleanShot X comes in. It’s a powerful screenshot and screen recording app for Mac that replaces the built-in screenshot tool. It feels as if the developers looked at the screenshot features in macOS and added everything that was missing.

Over the past few years, the app has added several new features I didn’t know I needed until it offered them. It has become one of my favorite Mac utilities, and in this article, I will show you its features that will convince you to buy the app instantly. 

Scrolling capture saves you from stitching screenshots together

One of the most frustrating limitations of macOS’s screenshot tool is that it can only capture what’s visible on your screen. If I need to capture a long webpage or a full chat history, I am stuck taking multiple screenshots and stitching them together. That wastes an unbelievable amount of time. 

CleanShot X solves this with its scrolling capture feature. I can trigger the scrolling capture, and CleanShot X automatically scrolls through the content and delivers a single image. I don’t even have to manually scroll the page if I don’t want to.

This feature alone saves me hours of time every month. If you have to deal with long screenshots, you should definitely try it out. 

Time delay capture lets you screenshot the impossible

Some screenshots are tricky to take because they require you to trigger something before capturing. For example, sometimes the on-screen feature you want to capture disappears as soon as you use a keyboard shortcut or click anywhere with your mouse. 

Sometimes, the on-screen elements appear for a short time, and by the time you hit the screenshot shortcut, they disappear. CleanShot X’s time delay capture gives me a few seconds to set things up before the screenshot is taken. I trigger the capture, put everything in place, and CleanShot X does the rest. 

It’s a small feature that solves a genuinely annoying problem.

Capture text from images with OCR

I love that CleanShot X has a built-in OCR function. It lets me capture text directly from any image or video on my screen. Although it happens rarely, I have come across websites that don’t let me copy content. With CleanShot X’s OCR function, that’s not an issue. 

I use this constantly when reviewing PDF documents with restricted permissions or watching a video on YouTube. It is far faster than typing things out manually, and it works surprisingly well. There are many apps that let you capture text with OCR, but since CleanShot X has this feature built in, I don’t need to install an extra app. 

Add beautiful backgrounds to your screenshots

If you share screenshots for work, tutorials, or social media, you know how plain a raw screenshot looks. CleanShot X lets me add beautiful backgrounds to my screenshots, turning a flat capture into something that looks polished and share-ready.

For backgrounds, I can choose from solid colors, gradients, or even my current desktop wallpaper. I can also adjust the padding and shadow, align the screenshot to the edges, and adjust the corner radius. It takes a few seconds and makes a huge difference in how professional your screenshots look.

Annotation tools that get the job done

While macOS’s screenshot tool lets you annotate your screenshots, the annotation tools inside CleanShot X are, in my opinion, the best available on the Mac. 

I can add arrows, text labels, shapes, highlights, and more. I can also change the weight and color of annotations. There are also multiple arrow styles I can choose from. I especially like the curved arrow style that lets me curve the arrows and make them pop. 

One of my favorite new additions is the “Highlighter” tool. It snaps to the text in a screenshot, which makes it really easy to highlight it before sharing. 

Then there’s the “Spotlight” tool that highlights your selection by darkening the rest of the screenshot. It’s perfect for drawing someone’s attention to a specific part of a screenshot. 

No matter what annotation tools you need, you can find them and more in CleanShot X. 

Hide sensitive information before you share

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I can choose to pixelate, blur, or completely black out the information. The best part is that I can also adjust the strength of these effects. It lets me blend in the hidden information so the blur doesn’t stand out from the rest of the screenshot. 

Video and GIF recording built right in

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It can record the entire screen, a specific window, or a custom region. It can also show my mouse clicks and keyboard shortcuts. I can record my computer audio, my microphone, and webcam video. 

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Quick share with cloud links

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Whenever I capture something, it opens a quick share overlay. I can use it to instantly upload my screenshots to CleanShot Cloud and grab a shareable link with a single click.

I no longer have to drag files into cloud storage, attach images to emails, or upload to third-party services. I capture it, click share, and paste the link. It is one of those workflow improvements that sounds minor until you use it every single day.

Capture beautiful screenshots with CleanShot X

CleanShot X has become one of my most dependable apps on Mac. In fact, all the screenshots you see in this article or any of my articles have been captured using CleanShot X. Yes, it’s a paid app, but it has paid its cost multiple times over with the time it has saved me. 

CleanShot X is available as a one-time purchase or through a SetApp subscription. If you want unlimited cloud storage, you have to pay for a monthly subscription. That will also get you advanced features like a custom domain and branding, password-protected link sharing, and more. 

For most users, the one-time purchase is more than enough, and it’s what I use. If you spend any time taking screenshots or recording your screen on a Mac, it is absolutely worth every penny.



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