Bug: Theme does not switch while active

[capital-G]

If KeepingYouAwake is active and the OS is set to automatically switch between light and dark mode, the OS does not switch the theme while active KeepingYouAwake is active.

I don't know if this is a KeepingYouAwake bug or a [caffeinate] bug - nonetheless probably worth to document.

[newmarcel]

That's indeed a tricky one. I've noticed that myself over the years too. There is sadly no public API to allow/perform this dark mode/light mode change.
It feels like macOS prefers doing these theme changes when you return from standby or when you close and open the lid again.
I will keep this issue open and continue doing some research. Maybe there are indirect ways of handling this.

Thank you for your feedback!