@spechter and @Cicciolinuks: Thanks for your suggestions.

I have added this request to the tracker:
Issue 2136 – Display caching status of directory contents
You can vote for it there.

It would be really awesome to have a toggle-button in the UI to:

1. turn caching on/off in an active session
   
2. Allow a use to know the status of caching on the screen.
   

Having to dig into the advanced options, before a connection, to change unexpected behaviour is a royal pain.

Otherwise WinSCP is an incredible tool, impeccably developed. Kudos to the developer. Which is why I was surprised to encounter this little annoyance!

To the developers: could be present a button that shows the state of every open directory? Cashed or fresh. Or when it was last time cached.

To improve the answer (that requires to follow 3 or 4 links to get the following):

1. If you don't have saved sessions, the login page will appear opening WinSCP, else click on "New session" on the session panel; the "Login" window will be open.
   
2. Then select one of your servers and click on "Edit". Finally you are in the Advanced Site Settings.
   
3. click on "Directories"; On the bottom there are few options, the one you want is: "Cache visited remote directories" AND/OR "Cache directory changes".
   

Of course this is for one server, you have to redo for others

Just turn off directory cache.

Yes, I know that I can manually refresh to work around this.

But I think it would be better if there were an option to have WinSCP automatically ensure that it displays a current directory listing whenever I open a directory. I understand that it might not be a desirable default because it would slow down opening directories containing many files.

I've noticed the same behavior. Try moving up one level, or more, and then refresh.

Is there some setting that makes winscp refresh the listing on browsing? Here's the scenario:

In winscp, I browse to some directory, say /usr/bin, do whatever, and then browse back to /usr.

Then, through another program (e.g. shell session) I create a file or directory in /usr/bin, or alternatively some process does the same.

Then in WinSCP, if I browse back to /usr/bin, I get the *old* listing – until I manually hit Refresh.

Any suggestions? Or should this be a feature request? If this doesn't exist, it could reasonably be lumped into the "automatically refresh directory after operation" setting (that is, browsing to a new directory could count as an operation)