Problem attaching XCode to Ableton

I don’t have Live installed on this machine so I can’t check, but it’s likely related to GateKeeper and the permissions Live grants.
Here’s Apples docs what they would need to do for this to work on recent MacOS versions:

Note:
To enable debugging a plug-in in the context of a host executable, the host can include the com.apple.security.get-task-allow entitlement if it also includes the Disable Library Validation Entitlement. Don’t disable library validation for executables that don’t host plug-ins because library validation protects them from loading untrusted code.

Recent Cubase versions set this accordingly, and Studio One will follow suite in their next update.
Here’s how to check from the command line:
codesign -d --entitlements - /Applications/whatever_app_you_want_to_check.app
the key to look for are:
com.apple.security.cs.disable-library-validation

com.apple.security.get-task-allow