Thanks for your answer. I understood that Contents/MonoBundle/ is not a valid code nesting site. However, Visual Studio for Mac uses this directory and there seems to be no way to change it. Is there a way to change this directory to Contents/Frameworks/ or is there another solution?

I took care of these points. not using the --deep option. Place only the code items in Contents/Frameworks and create Symlink to Contents/Frameworks in Contents/MonoBundle There were various files under the Contents/MonoBundle, and I used the otool -h -v command to investigate whether the file was a Mach-O object or not. Then I moved the file to Contents/Frameworks and created Symlink to Contents/Frameworks in Contents/MonoBundle. At this point, the app will launch normally. Then I signed it with the following command. codesign -v --force --timestamp --sign [signature code] \ /path/to/solution_directory/MyApp/bin/Release/MayApp.app/Contents/Frameworks/SQLite.Interop.dll codesign -v --force --timestamp --sign [signature code] \ /path/to/solution_directory/MyApp/bin/Release/MayApp.app/Contents/Frameworks/libmono-native.dylib codesign -v --force --timestamp --sign [signature code] \ /path/to/solution_directory/MyApp/bin/Release/MayApp.app/Contents/Frameworks/libMonoPosixHelper.dylib codesign -v --force -o runtime --timestamp --sign [signature code] \ --entitlements /path/to/solution_directory/MyApp/obj/Release/Entitlements.xcent \ /path/to/solution_directory/MyApp/bin/Release/MayApp.app But when I try to run the application, it crashes. This is the crash log. ~ Crashed Thread:				0	Dispatch queue: com.apple.main-thread Exception Type:				EXC_BAD_ACCESS (SIGSEGV) Exception Codes:			 KERN_INVALID_ADDRESS at 0x0000000000000000 Exception Note:				EXC_CORPSE_NOTIFY Termination Signal:		Segmentation fault: 11 Termination Reason:		Namespace SIGNAL, Code 0xb Terminating Process:	 exc handler [20121] VM Regions Near 0:-> 		__TEXT								 000000010005b000-0000000100479000 [ 4216K] r-x/r-x SM=COW	/Users/USER/*/MyApp.app/Contents/MacOS/MyApp ~ Is there something wrong with it?

Can you post the full crash report? Use a text attachment (the paperclip icon) so it doesn’t bloat the timeline. Thank you for your kindness... This is the full crash report. full crash report - https://developer.apple.com/forums/content/attachment/0731f8e2-8689-49b5-8823-0f327146e5cb

I was able to launch the app. Thank you so much for your thoughtful answers! I will ask questions here if I get a chance to do so again.

Thank you for your answer!! Hmmm, it's a bug that occurs in many places. I'm hoping Apple will fix it soon, but I'll try to do so by returning the bundle ID this time.

This is the result of executing the following commands on the terminal where the problem occurs. $ tccutil reset Accessibility [com.myapp] tccutil: Failed to reset Accessibility approval status for [com.myapp] After some research, I found a description that says /Library/Application Support/com.apple.TCC/TCC.db is corrupted when I get this kind of result.