@Lindon I find deleting the build (not Builds!) folder usually fixes this. Then I'll get the proper timestamps on both Debug/HISE Debug.app and Release/HISE.app
Projects > standalone > Builds > MacOSX > builds (delete this folder)
Also, sometimes Xcode builds HISE and the app size is around 100KB so I assume it failed but when I double click the HISE app it opens properly. Very strange.