Security researchers Talal Haj Bakry and Tommy Mysk disclosed on August 4, 2026 that Apple's iCloud Private Relay can be circumvented to reveal a user's real IP address through a series of flaws in the WebKit browser engine (mysk.blog). The researchers published a demo site, leaks.psylo.app, where anyone can test whether their IP address leaks while Private Relay is active. TechCrunch independently verified the leak on August 5, 2026 (TechCrunch).

Private Relay, available to iCloud+ subscribers, routes Safari traffic through two separate relays so that no single party sees both the user's identity and their destination. Apple describes it as a service that lets users "connect to and browse the web more privately and securely" (developer.apple.com). On iPad, Apple states it "hides a user's IP address and web browsing activity from network providers and websites" (Apple Support). Crucially, Private Relay is not a VPN. It protects traffic only within Safari, not at the system level, which means any browser or app traffic outside Safari's WebKit sandbox is inherently outside its threat model (TechCrunch).

The newly disclosed problem is different. The leak originates not in traffic outside Safari's scope but in three specific features within WebKit itself, which is the engine used by every browser on iOS due to Apple's platform restrictions. Because all iOS browsers are effectively WebKit wrappers, the flaws affect any iOS browser relying on Private Relay, not just Safari. The researchers did not name the three WebKit features publicly in their initial summary but described the mechanism as exploitable through a web page that triggers specific WebKit behaviors, causing the browser to make network requests that bypass Private Relay's dual-relay architecture (mysk.blog; 404 Media).

Mysk said the researchers chose not to report the issue through Apple's standard vulnerability disclosure channel. Past experience, he said, involved months of delays, inconsistent communication, and at times denial of an issue's impact (TechCrunch). The researchers instead published directly and built mitigations into their own privacy-focused browser, Psylo, which they say prevents the IP and DNS leaks. Those fixes shipped in Psylo version 1.3.1 (mysk.blog).

This is not the first time Private Relay's IP protection has been challenged. Researchers previously identified a vulnerability in Private Relay for iOS 15 that would let third parties circumvent its protections and obtain the user's IP address (Bitdefender). Apple's own documentation has acknowledged edge cases: the security notes for iPadOS 17.7.3 state that adding a website to the Safari Reading List may reveal the originating IP address to that website (Apple Support). Apple also notes that websites relying on IP filtering, monitoring, or rate-limiting may require a user's IP to be visible even with Private Relay enabled (Apple Support).

Apple did not immediately respond to a request for comment from TechCrunch regarding the new disclosure (TechCrunch).

The distinction between Private Relay's design intent and its real-world coverage matters for anyone who has assumed the feature provides VPN-equivalent protection. It does not, and Apple's marketing materials stop short of claiming it does. But the gap between what users infer from the iCloud+ privacy pitch and what the feature actually covers has been a recurring source of confusion since the feature launched. A privacy feature that can be defeated by a crafted web page, using the same browser engine it is designed to protect, is a meaningful limitation.

Worth flagging: Mysk's decision to publish without coordinated disclosure is a calculated trade-off. Responsible disclosure norms exist to give vendors time to patch before exploits circulate. But when a researcher has repeatedly encountered friction in that process, public disclosure becomes a form of leverage. The risk is that the disclosure site itself functions as a proof-of-concept that malicious actors can study. The mitigation for users in the short term is narrow: use a system-wide VPN if IP-level privacy is a genuine requirement, and recognize that Private Relay's protections are narrower than the iCloud+ branding implies.

The deeper structural issue is WebKit's universality on iOS. Because every iOS browser must use Apple's engine, a WebKit-level flaw affecting Private Relay has no browser escape hatch. Users cannot switch to a Chromium or Firefox build with a different networking stack. Apple's App Store policy, which mandates WebKit for all iOS browsers, concentrates the risk: one engine's bug becomes every browser's bug. That is a design choice with security implications that extend well beyond this single disclosure.