The "Debug / View Debugging" menu is always grayed out for me in Xcode 5 (and 6), even when the target is stopped at a breakpoint. How do I enable it?
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For me (Xcode 6 Beta and Beta two) the View Debugging options are only enabled in 32bit simulators (e.g. works when I use 'iPhone 5' but not when I am using 'iPhone 5s')
By adding support for 64bit (arm64) in your target, View Debugging is enabled for 64bit devices (iPhone 5s, iPhone 6 and iPhone 6 Plus)
In your target build settings make sure under Architectures that standard architectures is checked $(ARCHS_STANDARD), and under Valid Architectures you have arm64.