Password Twice

WinSCP always asks me for my password after I save changes to the first file I edit. When I login I enter my username and password, and after I edit my first file and save it, WinSCP asks for my password again, but never after that. Is that the expected behavior and if so, why? If I already authenticated, why do I have to do it again?

Great program by the way. :D

Make sure you have option Remember password of main session for background transfers enabled.

Perfect, thanks.

I can't find this option anymore. Has it been removed? - I'm using version 5.17.6

The option has been moved to the Security page:
https://winscp.net/eng/docs/ui_pref_security