I've used WinSCP for a long time, but the SSH recycle bin does something completely annoying. I don't know if this is a bug or a feature, but I'd love to see it removed.
If you have an SSH recycle bin and enable the "overwrite to recycle bin" option, and you are overwriting files to a partition which is not the same partition as the recycle bin directory is on (such as an external drive on /mnt/something or /media/something), an infinite loop of weird errors are given with the option to Abort, Skip, Retry, etc. Only "Abort" works, and then you have to go into settings and disable the "Overwrite to recycle bin" and start over.
I've had this issue on every SFTP connection I use, including on both LAN and Internet transfers.
Again, I'm not sure if this is a bug or a feature, but it is extremely annoying, and should be fixed IMO.
Thank you, Red