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I couldn't get Core Data with CloudKit working in Simulator. My current solution is... debug/develop with real device.

Found out what causes the issue... I did not install my system extension at all.Please check WWDC 2019 Sample code Filtering Network Traffic on how to install a system extension using "activationRequest" method.You can also find an article which gives us a high level description on those APIs Installing System Extensions and DriversBTW, big thanks to eskimo for his instruction here and the summary on Network Extension Framework Entitlements