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I updated my machine to: macOS Monterey Version 12.4 Xcode Version 13.4 (13F17a) iOS Version 15.4.1 (19E258) device real (iPhone 11) iOS Version 15.5 (19F77) device real (iPhone 11) I executed this command on host machine which is wirelessly connected to X code. $ automationmodetool enable-automationmode-without-authentication Setting up machine to allow Automation Mode without requiring user authentication... succeeded. $ automationmodetool Automation Mode is disabled. This device DOES NOT REQUIRE user authentication to enable Automation Mode. but I still get this exception Underlying Error: Timed out while enabling automation mode. My devices constantly requests password to enable UI Automation.