[tremon]

I still don't understand why [..] I have to toggle between pressing up or pressing down from the new command-prompt to access the previous commands.

It is because the shell history has its own completely invisible cursor, and the cursor is not reset after a command. So when you press <up> three times, then press <enter>, your history cursor is still at -3 (actually, -4). If you then want to move to command -2, you need to press <down> instead of <up>.

The real fun comes when you edit commands in your history (so press <up>, then edit the command line). I'm still not quite sure how Microsoft handles that.

[Someone]

Playing with the F7 key in your command shell (https://msdn.microsoft.com/en-us/library/windows/desktop/ms6...) will likely help you gain insight, if only temporarily.