404 Media

2026-08-05 13:46:30

Apple's ‘Private Relay’ Is Exposing Users’ Real IP Addresses

A series of issues in Apple’s web browser engine — the tech underlying all browsers on iOS — means that Apple’s iCloud Private Relay tool, which is supposed to hide a user’s IP address, in many cases doesn’t actually work. Instead, the issues mean a malicious attacker can set up a website to learn a Private Relay user’s real IP address, or that many websites have also already collected this information incidentally. The issues also impact OnionBrowser, an iOS app for browsing the web through the Tor anonymity network, the researchers who discovered the issues say.

The Private Relay leak is the second issue to recently impact Apple’s paid-for privacy products. Last month 404 Media reported a bug in Apple’s Hide My Email feature was actually revealing peoples’ real email addresses. Apple knew about that issue for more than a year before fixing it.

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Apple's ‘Private Relay’ Is Exposing Users’ Real IP Addresses

^{Joseph Cox (404 Media)}

404 Media

2026-07-28 14:06:28

Apple’s iMessage Scanning Flagged a Video of My Friend's Dog as Nudity

In a video my friend’s dog is laying on her back, her little paws in the air, while my friend rubs the dog’s chest. You can see most of the dog — who I’m not naming for very important privacy reasons — from her head to her belly. On closer inspection, you’ll notice the picture includes some dog nipples.

Apple’s iMessage thought this video was so inappropriate that it flagged the video as potentially containing nudity and blurred it. When someone else received the video over iMessage, the app displayed the message “This may be sensitive.” They had to purposefully tap to reveal the video of a dog laying on her back being petted.

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Apple’s iMessage Scanning Flagged a Video of My Friend's Dog as Nudity

^{Joseph Cox (404 Media)}

404 Media

2026-03-26 19:38:04

Apple Gives FBI a User’s Real Name Hidden Behind ’Hide My Email’ Feature

This article was produced in collaboration with Court Watch, an independent outlet that unearths overlooked court records. Subscribe to them here.

Apple provided the FBI with the real iCloud email address hidden behind Apple’s ‘Hide My Email’ feature, which lets paying iCloud+ users generate anonymous email addresses, according to a recently filed court record.

The move isn’t surprising but still provides uncommon insight into what data is available to authorities regarding the Apple feature. The data was turned over during an investigation into a man who allegedly sent a threatening email to ​​Alexis Wilkins, the girlfriend of FBI director Kash Patel.

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Apple Gives FBI a User’s Real Name Hidden Behind ’Hide My Email’ Feature

^{Joseph Cox (404 Media)}