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In this episode of Apple @ Work, I talk with Kate O’Neill about her book, What Matters Next: A Leader’s Guide to Making Human-Friendly Tech Decisions in a World That’s Moving Too Fast, and how it impacts today’s IT leaders.

After months of EU regulators breathing down its neck, Apple is finally seeing a happier kind of headline from across the Atlantic. And it comes courtesy of the new iPhone 16e.

If you’re Apple, this is the kind of internal document that you knew existed, but still hits hard. Especially in the middle of a global antitrust reckoning and internal… whatever the heck is going on in there.

A recently unsealed OpenAI file outlines the company’s ambitions for ChatGPT. In short? They’re coming for Siri with everything they’ve got.

WhatsApp is gearing up to launch a long-awaited feature: usernames. With usernames, users will be able to connect with others without sharing their actual phone number.

As we get closer to this year’s WWDC keynote, Apple has flipped the switch on its traditional X hashmoji.

The custom icon now appears automatically next to any post that includes #WWDC25, and it should look pretty familiar to anyone who’s seen Apple’s promotional art for the event.

Apple is said to be in talks with Major League Baseball to pick up streaming broadcast rights, especially focused on the Sunday Night Baseball games. The negotiations ensued after ESPN declined to renew its deal beyond the 2025 season.

The package of games that make up the former ESPN deal has drawn interest from Apple, NBC and others. It is likely the league will try to carve up the package into different buckets, to attract both a modern streaming audience and the eyeballs of traditional broadcast TV viewers.

The 2025 edition of the Fortune 500 is out, and Apple once again ranked near the top, while Walmart and Amazon remained firmly planted in first and second place, respectively, for the sixth straight year. Alphabet, meanwhile, was the most profitable company in the top 10.

Within the broader smart TV and streaming box market, Apple TV 4K is a fairly niche product. It’s found nowhere near the success of most Apple offerings like the iPhone and iPad. But a new deep dive at Ars Technica explains why Apple TV 4K is the only real streaming option for privacy-conscious users.

Apple has some major shake-ups coming to its iPhone lineup in the next few years, starting this fall when the iPhone 17 Air replaces the Plus model. My current plan is to replace my iPhone 16 Pro with the sleeker 17 Air model rather than a new Pro. Here’s why.

Back from 2005 to 2009, Apple used to have a neat little software feature called ‘Front Row’. It essentially allowed you to utilize an Apple TV remote with your Mac, and take advantage of a unique software interface for watching content. It didn’t last very long, but I think now could be a pretty unique time to reintroduce it.

MagSafe continues to be one of my favorite aspect of the iPhone. Like HomeKit gear, it’s easy to get carried away testing new accessories. But some products just do the job. Today, I’m revisiting two items I’ve kept in travel setup: the CLCKR Phone Holder & Grip and the Anker 622 Magnetic Battery, 5,000mAh Foldable Magnetic Wireless Portable Charger with Stand and USB-C. Neither is flashy, but both are incredibly useful day to day.

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Apple has been on an impressive streak with updates for its three-year-old AirPods Pro 2. You’d have a hard time finding another set of earbuds that’s received so many new features entirely via software. Among the most recent additions, Hearing Protection stands out as AirPods Pro’s most ahead-of-its-time feature yet.

We’re just one week away from WWDC 2025, which kicks off on Monday, June 9 with Apple’s keynote. Ahead of the festivities, Apple has started teasing WWDC25 with a new tagline: “Sleek peek.”

“A week of technology and creativity. All online and free,” Apple says.

Apple Intelligence doesn’t yet offer a proper chatbot experience, but it turns out Writing Tools can be coerced into behaving as one.

Bloomberg reports that we can look forward to macOS Lake Tahoe, aka macOS 26, when Apple unveils its new operating systems at next week’s WWDC.

macOS Lake Tahoe will of course include some beautiful new wallpaper, but if you want to get in the mood ahead of time, we’ve rounded up some wallpaper you can use today …

Apple TV+ kicks off the summer with a June release slate that offers a little something for everyone. There’s a Ted Lasso-style sports comedy, new children’s programming, a Sydney Sweeney-starring horror film, Bridgerton-like historical romance, and a prestige crime thriller from the team behind one of Apple’s best. Among Apple’s full June TV+ lineup, here are the three biggest shows to look out for.

While Apple regularly gets lambasted for lack of promotion for its streaming service, Apple TV+, the company seems to be trying harder in recent weeks. It just dropped a ‘New for June’ sizzle reel, hyping what users can expect to stream on the service this month.

The new premieres include comedy series Stick, movie Echo Valley, season two of The Buccaneers, and Taron Egerton drama Smoke. Here’s everything new on Apple TV+ in June …

The leisurely pace of Apple’s AI efforts has come under increasing fire, with the company accused of being behind the curve. But a new study on the dangers of AI chatbots suggests that other companies are not being cautious enough.

OpenAI had to recall a recent ChatGPT update, after it tried too hard to agree with users, resulting in an experience which was both absurd and awkward – but the problem is bigger than that …

Jeff and Fernando talk about Apple’s impressive history with accessibility, including our favorite accessibility tips and tricks, and upcoming accessibility features in iOS 26!

Sponsored by Bitwarden: Check out Bitwarden Password Manager, featuring an Apple Watch authenticator integration, secure autofill on Safari and iOS apps, and enterprise-grade security tools that help you manage credentials with confidence.

9to5Mac Overtime is a weekly video-first podcast exploring fun and interesting observations in the Apple ecosystem, featuring 9to5Mac’s Fernando Silva & Jeff Benjamin. Subscribe to Overtime via Apple Podcasts and our YouTube channel for more.

Apple last week announced that iPads have joined the Self Service Repair program, enabling owners and independent repair shops alike to get access to manuals, tools, and parts.

The company said it was excited to expand the program to iPads, but a closer look at the details reveals both good news and bad …