First of all, not sure if the forum is the best place to ask a putty-winSCP questions, as probably is not really related to OpenNTM. Also, let me say I am a newcomer to linux, so probably I am also not the best person to answer, so just to guess, my bits.
I have my linux setup for putty, and instead of using winSCP I have using the “pscp.exe” command to transfer files without any problems.
I have installed the WinSCP and I have been able to transfer files from my client to the linux box and from the linux box to my client. But not using Amazon AMI. Not sure if it makes any difference as the port for ssh is the same for the file transfer.
Once i have installed I can drag and drop. just for you info.
Maybe you can try “pscp.exe” or ask for help in the WinSCP or Amazon support community.
have a nice day