Thanks for the quick reply! I was missing the NSPanel bit! I forgot to mention that I added the Application is agent (LSUIElement) key to the info.plist which seems to be equivalent to your first point. Now everything seems to work as you've stated. I tested those scenarios as well and it always stays on top!

I tried the solution today and would like to post a correction: Using the --relative-to-command-file or -c flag will then expect a Python module name, which needs to be located directly next to the command file. Demonstrating with examples: $(SRCROOT)/.lldbinit with the following content: command script import --relative-to-command-file ./lldb/type_formatters.py Will result in an error: error: module importing failed: Python does not allow dots in module names: ./lldb/type_formatters $(SRCROOT)/lldb/.lldbinit with the following content: command script import --relative-to-command-file type_formatters Will result in a successful import $(SRCROOT)/.lldbinit with the following content: command script import lldb Will succeed if $(SRCROOT)/lldb is a Python module, denoted with a __init__.py file at $(SRCROOT)/lldb/__init__.py Further python modules then can be imported with command script import <module_name> which live under $(SRCROOT)/lldb

I didn't know about script import's --relative-to-command-file flag. This is exactly what I was looking for. Thank you!