Does SketchUp have the “com.apple.security.get-task-allow” entitlement set?
Recent versions of macOS have made it impossible to debug any ‘native code’ plugins without that:
You cannot attach a debugger unless one of the following applies:
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The host application has “com.apple.security.get-task-allow” to enable debugging.
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The private developer key used to sign the host application is in the user’s keychain.
This would allow (some) SketchUp employees to debug plugins, but nobody else. -
You have disabled System Integrity Protection using crsutil in Recovery mode.
This does not appear to be supported, Apple have implied this will be removed ‘soon’.
It is unclear why Apple have such a dislike of software development on their platforms.