What I am describing is in no way a critical bug, but it's something I've experienced since a long time, something that's just not really right: a normally nice feature, that isn't working properly in a certain condition. It is about the UI.
Suppose we have navigated into a folder /www/cms/js/. This path appears over the folder overview. When we click on 'cms' on that line, WinSCP takes us to that folder (i.e. the parent folder of where we were). Once there, the 'js' folder is highlighted with a dotted border around it, as if to tell us "that's where you were just before". That's handy.
Now, suppose that we didn't click on 'cms' but we clicked on 'www', in other words, we move up two levels instead of one. Once there, no specific folder is selected, which is fine. Except if this 'www' folder has its own 'js' folder -- so there's a 'js' folder in both the 'www' and the 'cms' folder. In that case, when you jump from /www/cms/js/ straight to /www/, the 'js' folder inside the 'www' folder will be highlighted. This time however, that is not where we came from. I understand why WinSCP highlights it, but it's wrong. If highlighting anything, it should be highlighting the 'cms' folder (i.e. the first part of the path that we come out of), but in any case not the 'js' folder, because we weren't anywhere near there. It just happened to have the same name as the folder that we did come out of.