Request times out with iCloud Private Relay: Why?

We have our own backend, running on our own server.

When iCloud Private Relay is enabled, the requests to the server time out.

How can we find out what precisely is failing? TLS 1.3 is enabled on the backend

finished with error [-1001] Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo={_kCFStreamErrorCodeKey=-2102, NSUnderlyingError=0x281b0a3d0 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={_kCFStreamErrorCodeKey=-2102, _kCFStreamErrorDomainKey=4}}, _NSURLErrorFailingURLSessionTaskErrorKey=LocalDataTask <CBAE9DA5-9988-4E55-A732-B759842E411F>.<1>, _NSURLErrorRelatedURLSessionTaskErrorKey=(

    "LocalDataTask <CBAE9DA5-9988-4E55-A732-B759842E411F>.<1>"

), NSLocalizedDescription=The request timed out.,
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The problem was the local firewall …

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The problem was the local firewall …

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How can we find out what precisely is failing?

For others reading this, one way to diagnose what is happening here is to take a packet trace for traffic entering the network, on the server side. This test, of course, would be recommended in a staging network, but you would be able to see the traffic coming from the Egress proxy and be able to see if it's having issues passing through your network and if it is making it to the downstream systems.

Matt Eaton
DTS Engineering, CoreOS
meaton3@apple.com
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