aruhela wrote:
Since a user has already logged in to the remote server, therefore, I expect WinSCP not to ask the authentication again while doing file modification. If not possible for some reason, then, for the ease of users, WinSCP should use the already stored password and only ask for the token to be entered.
Files saved in an editor are put to a transfer queue for an upload. The queue (must) uses a different connection, so it needs a new authentication. WinSCP actually remembers the token (assuming it's a password) and re-tries it for the authentication. That fails (I assume the token is one-time only) and WinSCP restarts the authentication from the scratch, not using a stored password, as it does not know what caused failed authentication (which of the two "passwords"). Try turning off
Remember password for duration of the session:
https://winscp.net/eng/docs/ui_pref_security