I tested this on 4.1 and 4.4dev3, with dwm X11 (linux)
I have the new autoload enabled, and the 2 new boolean settings are by default On (enabled), and Screen is 0.
I also tried enabling and disabling Borderless.
I don't have any errors or warnings, but I don't have the above result (expected tbh because dwm)

When ran with 9 windows, 5 of them are tiled, 4 are left as-is ( laid out manually for illustration ):

Testing further, it seems like only the first 5 windows are tiled, the rest are left as-is.

Looks like 5 windows is the cap as Godot's Debugger only tries 5 times to find a free port for a client to bind to.

https://github.com/godotengine/godot/blob/36e6207bb48fafd43b98a458d0c461ad982b4e68/editor/debugger/editor_debugger_server.cpp#L87

You'll notice you only get 5 Debug Sessions also in the editor.

An alternative would be to piggy back off an established multiplayer peer connection and not use the EditorDebugger

Ditched the whole EditorDebuggerPlugin communication system for good old lock files.

Making borderless false by default as there are inconsistent results for now.

godotengine/godot#93472

Updated the lock detection to do an initial wait, then check for a while if any new locks show up. This way, if startup is slow, we have a way better chance to detect late arrivers. If startup is fast, the loop can terminate early, as no new locks are found.