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iOS 27 bill splitting, new hardware waiting on new Siri, final WWDC expectations

Benjamin and Chance talk about the late-breaking iOS 27 rumors, including a new bill splitting feature for the Wallet app, as well as give their final expectations for next week’s WWDC announcements. Apple fixes Mayo’s iPhone Air battery glitch, and new Apple TV and HomePod models are apparently in the final testing stage. Also, code references reignite ideas about new cheaper (or free) tiers of Apple Music. 

And in Happy Hour Plus, on the eve of iOS 27, we give our 1 year retrospective on how iOS 26 has fared in the wild. Subscribe at 9to5mac.com/join.

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Security Bite: DeepSeek trending among US firms as low-cost AI alternative, what could go wrong?

DeepSeek privacy under investigation in US and Europe | App seen on an iPhone

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A rather alarming new report from financial services company Ramp shows DeepSeek catching on with US firms looking for cheaper alternatives to Anthropic and OpenAI. In its June 2026 series covering all of last month, the Chinese AI company ranked first among SaaS vendors for breakout growth relative to size across Ramp customers.

Needless to say, the security implications here are quite alarming.

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9to5Mac Daily: June 4, 2026 – iPhone Ultra rumors, Siri servers

9to5mac daily podcast

Listen to a recap of the top stories of the day from 9to5Mac. 9to5Mac Daily is available on iTunes and Apple’s Podcasts appStitcherTuneInGoogle Play, or through our dedicated RSS feed for Overcast and other podcast players.

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OpenAI says ChatGPT’s memory feature is getting smarter and coming to free users

ChatGPT’s memory feature allows it to learn about you and remember your preferences over time. Memory gives ChatGPT useful context for natural interactions that don’t need start from scratch each time. OpenAI has released new details on how ChatGPT’s memory feature is getting smarter and coming to free users for the first time.

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I built the ultimate Cosmic Orange iPhone everyday carry [Video]

When Apple unveiled the Cosmic Orange iPhone 17 Pro and Pro Max, I was a bit skeptical. Apple usually reserves more “professional” and dull colors for the Pro models and the more vibrant colors for the regular iPhone lineup. But as someone who loves orange as a color, I went with the 17 Pro in Cosmic Orange. After using it since day one, I can easily say this is my favorite iPhone color variation in a long time. So, naturally, as time went on, some of my favorite accessories began to color-match the Cosmic Orange iPhone, and I had to build an everyday carry around it. These accessories not only complement the Cosmic Orange finish perfectly but also solve real problems, earning a permanent place in my EDC.

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Deals: AirPods Max 2 hit Amazon all-time low, AirPods Pro 3, iPhone Air $149 off, Watch bands from $15, more

Joining AirPods Pro 3 at one of the lowest prices to date and AirPods 4 at nearly 25% off, today’s 9to5Toys Lunch Break is headlined by Apple’s new AirPods Max 2 hitting the best price ever. Best Buy has indeed launched a major 4-day Apple sale event, but these AirPods and MacBook deals are even lower, while all brand new condition iPhone Air models just dropped back to all-time low pricing at $149 off. Head below for a closer look and even more.

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