Apple may have finally fixed Siri
Plus: Meta gets creepier, a travel site that impressed me, and a rideshare trick to save money
Greetings and welcome to another edition of the Rich On Tech Newsletter!
This week I was in Cupertino for Apple’s Worldwide Developers Conference. I’ve been covering Apple events for 15 years, and it’s still quite the experience.
If you think the iPhone and its software are polished, it doesn’t stop there. Apple Park is filled with meticulously engineered buildings, beautifully manicured landscapes, and yes, actual apple trees. (They grow a lot of fruit on campus.) There’s also the Apple Park Visitor Center, complete with a store and café that attract a steady stream of visitors every day.
Of course, all of that was just the backdrop for the main event: WWDC 2026, Apple’s annual conference for developers. I was especially interested to see how Apple would finally deliver on its promise of a smarter Siri. After spending the week with the new software, I think they got it right.
We’ll get into all of that in a moment, but remember: this was a software event. The new iPhones, and the long-rumored foldable iPhone, are still expected to arrive in September.
Speaking of September, I have a highly scientific method for predicting Apple event dates, and my guess right now is September 8. How do I know? I can’t tell you. Let’s just say after 15 years of covering Apple, you start to notice a few patterns.
We’ll see if I’m right.
One quick tip before we dive into WWDC: I took a lot of rideshares during this trip, and it reinforced something I’ve learned over the years. Always keep both Uber and Lyft installed on your phone.
For nearly every ride I took for this trip, Lyft was considerably cheaper than Uber. On other trips, I’ve seen the exact opposite. Yes, it’s a bit annoying to open both apps and compare prices, but it takes just a few seconds and can save you a decent amount of money.
Apple may have finally fixed Siri
The keynote is what everyone watches, but that’s only part of WWDC. After the presentation wraps up, Apple spends the next day and a half giving reporters hands-on access to the new software and the people who built it.
One of the first sessions I attended was a smaller media briefing with Craig Federighi, Apple’s software chief. He spent a good chunk of time explaining exactly how the new Siri AI works and, just as importantly, how Apple plans to keep it private.
As for the keynote itself, it felt a little different this year.
Normally, Apple spends nearly two hours walking through the new features of every platform. But this time, they focused mostly on Siri AI and iOS 27.
Apple says apps will launch faster, photos will load quicker, and AirDrop transfers can be up to 80 percent faster. The company basically went through the operating system looking for ways to make the iPhone feel snappier.
The good news is that iOS 27 will run on every iPhone that supports iOS 26 today. That means iPhone 11 and newer, plus the second-generation iPhone SE and later. That’s seven years of software updates, which is pretty great.
But let’s be honest. The reason everyone was paying attention was Siri.
Apple is calling the new version Siri AI. I’ve already got it on my iPhone and even in it’s unfinished beta state, I think it’s the upgrade many have been waiting for.
The voice assistant has been rebuilt from the ground up. Think of it as Siri with the conversational abilities we have come to expect from tools like ChatGPT and Gemini.
The difference is that Siri understands what’s already on your phone.
With your permission, it can access your emails, messages, photos, notes, calendar and more. It can answer questions about your life, not just questions about the world (and those have gotten better too!)
You can ask things like:
What restaurant did my wife text me about last month?
What books did my friend recommend?
When is my next dentist appointment?
Those are the kinds of things that normally require searching through multiple apps. Siri can now do it instantly. It’s almost as if all of the information you’ve been storing in iCloud over the past decade is suddenly unlocked in a super easy to access.
The other thing Apple is betting on is privacy.
Apple says as much processing as possible happens directly on your device. If Siri needs cloud computing power, requests are handled through Apple’s Private Cloud Compute servers, which Apple says processes the request and then immediately discards the data.
Apple is late to all of this and sure, Google and OpenAI can do similar things, but there are two big differences - Siri AI is built in to the phone many are already using most, and privacy is a big part of the appeal.
Apple says Siri AI will arrive in beta later this year, but it won’t be available on every phone that gets iOS 27. You’ll need an iPhone 15 Pro, iPhone 15 Pro Max or newer to get the full experience.
If you thought Apple had fallen behind in AI, I think this week’s announcements changed that conversation. Apple may not do things first, but at this point, it feels like Siri AI is the future we expected from the iPhone.
Other iOS 27 features I actually liked
While Siri was the star of the show, there were plenty of smaller features that stood out.
One of my favorites is the ability to create Shortcuts using plain English. If you’ve ever tried building a Shortcut before, you know it can feel like programming. Now you can simply describe what you want. I told it to create a shortcut that texts my wife when I’m headed home and includes my ETA. It built it for me in seconds.
The Photos app is getting some useful AI tools. One called Extend can generate additional image beyond the edges of a photo when you need more room for a crop. Another called Spatial Reframing lets you virtually adjust the camera angle after the picture is taken. Think of it as moving the camera slightly left, right, up, or down after the fact. It’s pretty impressive, I’m just not sure I’d ever actually use it.
Parents will appreciate Apple's redesigned Screen Time controls. The new system gives families more control over when apps can be used and how much time kids spend in different categories like social media, games and video apps. You can now set Time Allowances for entire groups of apps, instantly pause a child's device, or grant unlimited time for the day, say during a long flight, without having to adjust their regular schedule or limits.
A few other changes I noticed: alarm volume can finally be controlled independently from the rest of the system volume, FaceTime gets a dual-capture mode so you can show what you’re looking at while keeping your face on screen, and shared iCloud photo albums now work with Android and Windows users, who can contribute photos, too.
🔗 Want even more? Here’s a detailed list of all of the expected improvements.
Facebook and Instagram are about to get a lot creepier
You know how ads on Facebook and Instagram seem to know exactly what you’ve been shopping for?
Starting next month, Meta will begin using information it receives from other websites and apps to personalize not just ads, but also the content that appears in your Facebook and Instagram feeds, along with responses from Meta AI.
The company says it’s not collecting any new information. Instead, it’s expanding how it uses data already being shared through tracking tools embedded on millions of websites and apps.
When I checked my own account, I was surprised to see activity being shared from companies including Nike, DoorDash, OpenTable, Spotify, Peacock and Redfin. Peacock alone had logged more than 1,100 interactions.
Want to see who’s sharing your activity with Meta?
Open Facebook or Instagram → Profile → Menu → Accounts Center → Your information and permissions → Activity from other businesses (or “Your activity off Meta technologies” if you haven’t received the update yet).
If you’d rather Meta not use that information to personalize your feed, ads and AI experiences, go to the same screen and select:
Don’t allow us to use this activity to show you relevant content.
Keep in mind that if you don’t see the “Activity from other businesses” option yet, that’s normal. Meta says the feature is still rolling out, so it may take some time before it appears on everyone’s account.
Sponsored by Surfshark
One category of tech question I get all the time is about VPNs.
Do I really need one? What’s the best VPN? Is a free VPN okay? Will it make me safer online? Can it help when I travel?
The answer is that a VPN isn’t magic, but it is one of the easiest ways to add an extra layer of privacy and security to your online life.
A VPN creates an encrypted connection between your device and the internet. That can help protect your information when you’re using public Wi-Fi at hotels, airports, coffee shops, and other places where you don’t control the network.
Many of the VPN questions I receive come from travelers. People want to know if they should use one when they’re on hotel Wi-Fi, visiting another country, or working remotely. My answer is usually the same: a reputable VPN is a smart tool to have in your digital toolbox.
That’s where this week’s sponsor, Surfshark, comes in.
Surfshark works on unlimited devices under a single account, which is especially useful if you’re juggling phones, tablets, laptops, and streaming devices. Beyond the VPN itself, Surfshark also offers tools that can alert you if your personal information appears in a data breach and help reduce the amount of personal information data brokers collect about you online.
Not sure how exposed your information is? Surfshark has a quick online quiz that shows how much of your digital footprint may be at risk and what steps you can take to improve your privacy.
🔗 Take the quiz here and thanks to Surfshark for supporting the newsletter.
Tech Tidbits
AT&T now lets you buy a cellular day pass for your iPad for $3. You don’t need to be an AT&T customer. If you’re traveling and just need data for a day or two, you can activate it instantly. Just make sure you have a cellular iPad, not a Wi-Fi-only model.
Instagram now lets you rearrange the photos on your profile grid. Just press and hold a photo, then choose “Reorder Grid.” I have a feeling some people are going to spend way too much time on this.
The popular Watch Duty app, which became a must-have during Southern California’s wildfire seasons, is expanding into flood alerts.
Mint Mobile increased data allowances on plans without raising prices. The 5GB plan now gets 6GB, the 15GB plan gets 17GB, and the 20GB plan gets 23GB. It’s not a huge change, but I’ll take more data for the same price any day.
Got your own phone? Google Fi is offering 50% off select unlimited plans for 12 months when you bring your device. It’s one of my favorite options for international travelers, and it includes some nice perks, including connectivity for compatible smartwatches, tablets, and laptops.
A travel site that actually impressed me
On last week’s radio show, I had travel expert Ben Komenkul of Ben’s Big Deal on to share some of his favorite travel websites. One of the sites he mentioned was Gondola.
I actually tested Gondola when it first launched, but back then it was focused on scanning your email to find your travel reservations, loyalty programs and points balances. I wasn’t a huge fan of connecting my email account, so I never really gave it much thought after that.
This time around, I took another look and found a feature I really like: hotel suite search.
If you’re traveling with a family, you know how frustrating it can be to find a room that’s actually big enough for everyone. Too often you’re forced to book two rooms or spend way too much time digging through hotel websites trying to figure out which properties have suites that will work.
Ben mentioned that Gondola lets travelers search hotels by specific features that matter to them, whether that’s a great pool, a gym, or something else. What stood out to me was the ability to search specifically for suites across major hotel chains and compare options in one place.
I’ve tried Suiteness before, which is another useful site for finding suites and connecting rooms, but I often find myself looking at very expensive properties. Gondola seems to surface a bigger mix of options across the major hotel brands.
Another neat feature? Their deals page. You can browse through the best hotel points redemptions around the world for a good use of your points!
One thing I still don’t understand: why is booking connecting rooms so difficult in 2026? Some hotel chains make it easier than others, but too often you’re still forced to make a request and hope for the best.
With all the technology available today, it feels like this should be a solved problem by now.
Q&A: Scam search results
Steve in Orlando, FL (podcast listener) writes…
Q: My 88-year-old mother keeps running into serious trouble when clicking on Google search results. Her screen will suddenly start flashing with loud alarms playing through the speakers, prompting her to call a fake “Microsoft Support” number. I’m not sure if she’s clicking on sponsored links or something else. What search engine do you recommend that would help her avoid these scam results entirely?
A: Those flashing “Microsoft Support” alerts are a common scam tactic called malvertising. Scammers buy advertising space on search engines and use alarming pop-ups to trick people into calling fake tech support numbers.
Instead of switching search engines, I’d install a free ad blocker like Ghostery on her browser. It will block many of these sponsored scam links before she ever sees them.
I’d also teach her a simple escape hatch: if one of these fake alerts takes over the screen, press Alt + F4 on Windows to immediately close the active window. No clicking. No calling the phone number. Just close it and move on.
One final tip: remind her that legitimate companies like Microsoft, Apple, Google, or Amazon will never display a pop-up telling her to call a support number because her computer is infected. If she sees a message like that, it’s almost certainly a scam.
Feedbag
Levi writes: “I really think you should start ending your TV segments with, ‘And now you’re Tech Rich!’ It seems like a missed opportunity for a great one-liner. Love the segments, though!”
Marcy says: “I enjoyed your plug for the library system. I don’t get TV reception by choice and order all my Libby books and DVDs online. Every week or so, I stop by the library to pick up and drop off items while I’m running errands. One feature people may not know about is Link+, which is available through the San Diego County library system. If your local library doesn’t have what you’re looking for, Link+ connects you with libraries across California. You can request an item and have it sent right to your local library for pickup. It couldn’t be easier.”
Melissa writes: “Thanks for the newsletters, I share them. YOU ROCK!”
Frank from Bradbury asks:
“Rich, AI may replace your programs! AI On Tech must know more than you?”
Perhaps, Frank… but does a robot have a soul and a sense of humor? I don’t think so. And if it does, a human probably programmed it that way.
That’s going to do it for this issue of the newsletter.
Before I go, you’ve got to love technology when it protects us from ourselves.
The other day, I was heading to a doctor’s appointment and didn’t want to pay for parking in the garage. If you’ve parked in Los Angeles lately, you know why.
I found an open spot on the street and sat in my car for a few minutes checking email before my appointment. When I got out, I started to put change (yes, change!) in the parking meter when I noticed a warning that said “Do Not Park, Tow Away Zone.”
Sure enough, I looked up and saw the sign. That’s why the spot was open.
By some other miracle, I found another space nearby. But this one was on a busy street. When I went to open my car door, it wouldn’t budge.
At first I thought something was wrong with the car. Then a message appeared on the dashboard that basically said:
“We stopped your door from opening because a vehicle or cyclist was approaching.”
I had never seen that feature activate before, but I smiled.
Pretty impressive when technology can save us from ourselves.
Don't forget to tune into the Rich On Tech radio show. We're live Saturdays from 11 AM to 2 PM on KFI AM 640 in Los Angeles. You can also stream the show live, catch the podcast anytime, or listen Sundays at 8 PM Eastern on 710 WOR in New York.
Have a great weekend!
Rich