Is this about WinSCP GUI or script? What version of WinSCP?
I have WinSCP and a few Pis and connect to the Pis by SCP.
I am finding that some passwords, whilst being useable with the Pis are denied access by the WinSCP. An example that won't connect is: ]Mt'ay.8D2l$6x6 whereas M_yBW]l_6 is accepted on another Pi. I'm happy that I have them properly configured on the Pis. If I change the one to a completely alpha-numeric password without any special characters WinSCP has no issues connecting but obviously the password is weaker. I can't go for alternatives to passwords as I also use an android phone to "speak" to the Pis.
Any thoughts? Is this a WinSCP issue? How can I use stronger passwords without having the use of "string.punctuation" to add to the mix?