I have literally never had macOS' restore session feature work correctly. It's so bad that I just decline it.

It will try to start up the applications I least care about; meanwhile ignoring the actual context I desire, which just slows me down more.

These days, Windows will try to recover your context, but the implementation (like many other modern features like display scaling) is dependent on the app. As far as I've been able to tell, roughly most Microsoft and Electron apps will recover their states on reboot; most other apps won't.

Like a sibling commenter, I've found this pretty hit-and-miss too.

Something like Outlook or OneNote will restore its state reasonably well, as will Safari/Chrome/Edge/Firefox. Others, like Activity Monitor, Enpass, and iTerm2, decide to "helpfully" open a window for me even though the previous state was "running with no windows open" (which is perfectly valid for many applications).