I'm doing the same and it works for me.

I have sent you an email with a debug version of WinSCP to the address you have used to register on this forum.

I connect to my server
At this point "Restore Selection" is disabled
I select two files (for example) by holding the control key
At this point "Clear Selection" is enabled but "Restore Selection" still not
I drag and drop both files over to the server
Both files are unselected
Restore Selection" is still disabled

Can you describe step by step, what you are doing to select and transfer the files, so that after the transfer the command is disabled?

hm.. unfortunately that option is disabled. Do you know why it would be disabled?

Indeed, WinSCP unselects the files as they are transferred. You can restore the selection by going to Mark > Restore Selection.

Just started using WinSCP and I quite like it but there are a few things not working the way I like and I'm hoping there's a setting I can enable or disable.

If I select multiple files in my local browser and then drag them over to the remote browser, WinSCP immediately unselects all the files I had selected. This is annoying because I frequently have to copy those same files to multiple directories.

Is there a setting that's causing them to be unselected, or is there a setting I can enable to keep them selected?

I thought maybe the local browser was automatically refreshing but I only see such an option for the remote browser (which I've disabled) and I thought that might be it because I have synchronized browsing enabled so I thought it might be refreshing both panels, but that didn't make any difference. Anybody have any other ideas?