Either I'm missing something or you contradict yourself.
The GUI log shows that you server needs both
private key and password to authenticate. And as the private key is encrypted, WinSCP needs also the private key passphrase.
! 2022-05-31 23:45:28.530 Authenticating with public key "xxxxxxx"
. 2022-05-31 23:45:28.565 Prompt (passphrase, "SSH key passphrase", <no instructions>, "Passphrase for key "ecdsa-key-20210322": ")
. 2022-05-31 23:45:32.163 Sent public key signature
! 2022-05-31 23:45:32.218 Further authentication required
. 2022-05-31 23:45:32.229 Further authentication required
. 2022-05-31 23:45:32.229 Server offered these authentication methods: password,firstname.lastname@example.org,keyboard-interactive
. 2022-05-31 23:45:32.229 Attempting keyboard-interactive authentication
. 2022-05-31 23:45:32.279 Prompt (keyboard interactive, "SSH server: password", "Enter password for xxxx", "Password:")
. 2022-05-31 23:45:32.279 Using stored password.
So it should not be surprising that the script "is still asking for another password"
, if you didn't provide any.
And then you wrote that you have tried to use same password stored in the Session Manager
– so what password, if you seem to imply that the GUI does not need any?
Apparently, you didn't use the same password as in the GUI.
Have the GUI generate a script template for you to make sure you have all settings identical:
You still might need to add the