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Deals: AirPods Pro 3, AirPods Max 2, Apple Watch from $219, black Trail Loop, MacBook Air, more

Today’s 9to5Toys Lunch Break is headlined by some of the best AirPods deals of the year – AirPods Pro 3 down at $199, AirPods 4 nearly 25% off, and the best price ever on AirPods Max 2. Alongside the most affordable Apple Watch Series 11 down at $299 ($100 off) and Apple Watch SE 3 down at $219, we also have a super rare discount hitting Apple’s latest black Ultra Trail Loop today and Spigen’s Athlex Trail Loop-style Apple Watch band at $20. Just be sure to also scope out these M5 MacBook Air models still up to $270 off. Head below for a closer look.

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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.

Sponsored by CardPointers: The best way to maximize your credit card rewards. 9to5Mac Daily listeners can exclusively save 30% and get a $100 Savings Card.

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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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