Is it possible to have two Entitlements.plist files so that the one which the debugger can attach is associated with the debug build configuration whilst the one without would be associated with the release configuration?
Sure. In the build settings, you can specify a different Entitlements plist file for specific build configurations. Just set the appropriate one for Debug and a different one for release/distribution etc.
The settings is called "Code Signing Entitlements" or "CODE_SIGN_ENTITLEMENTS" depending on whether you have show names or titles set.
Just specify the name of the Entitlements.plist file you wish to use, eg:
Entitlements-Debug.plist
or
Entitlements-Distribution.plist
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