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I'm asking myself if it is possible to send custom requests (including custom headers) via the iCloud private relay, as I could do it with a normal VPN ?

If not, is there any program made to send custom requests from safari such as chromedriver does with chrome, in the goal to pass by the private relay ?

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    Commented Mar 30, 2022 at 22:20

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In beta - iCloud Private Relay is transparent and offers no configuration options. What differentiates Apple’s offering from the others I have evaluated is there are two levels of indirection where Apple would hopefully strip away custom requests by design.

The technical / developer level details how it uses UDP / QUIC are also documented online:

Perhaps if you explained your end goal in using custom headers, we could elaborate more.

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