CI failure's unrelated to the changes. I'm looking into it.

The same happened for me it was because of click latest version and make.py when i installed old stable version it worked
uv pip install click==8.1.7

Did click make breaking changes in a minor version or something? We're pinning a specific typer version so this is a little unexpected:

I found these two reasons see if they are useful

Replace typer[all]==0.12.5 with typer==0.12.5, because the all extra was removed in 0.12.0 and since 0.12.1 the base typer package already includes the default optional dependencies and the typer command by default. The warning is expected in 0.12.x when requesting a non-existent extra and can be safely resolved by dropping [all] from the requirement.

(from Click changelog)

Click 8.3.0 (2025-09-17) changed flag handling: "Improved flag option handling: Reworked the relationship between flag_value and default parameters ... The default parameter value is now preserved ... Exception: flag options with default=True maintain backward compatibility..."
In other words, Click 8.3 tightened how default, flag_value and is_flag interact and now rejects creating a "secondary flag" (the automatic --no-flag) for an Option that Click treats as non-boolean.
Our repo pins Typer to 0.12.5. Typer 0.12.5 builds Click Option objects in the old, permissive way. With Click 8.3, Typer’s created Option sometimes fails Click’s new validation and triggers that TypeError.

Yes, I have already joined in the python arcade discord server.