Authentication Progress

If you are using password authentication, you can enter your password directly on Login dialog. Otherwise WinSCP will prompt you once a server asks for it. You will be prompted again, if you enter invalid password. Also note that most of the servers will “prompt” for password when you use invalid username, not to allow attacker to learn if particular account exists.

If you are using public key authentication with encrypted private key you will be prompted to enter passphrase for your key.

As the server can generally prompt for anything, the answer can be quite long and may not be even secret. For the reason you can make it visible by unchecking Hide typing, so you can easier type it.

During authentication the server can issue authentication banner. It can contain various information, generally regarding security and server usage. After reviewing the text, press Continue button to continue.

If you want to avoid seeing the banner each time you login, check Never show this banner again. It will make WinSCP ignore the same banner for the particular account and server the next time. However if the banner content changes you will see it again. Suppression of banners can be restricted by system administrator.