It seems that winSCP has problems parsing file information. An eror appears when I enter a directory and no files are shown. When I log onto the server with other SCP clients I have no problems (though other clients are not as nice to use as WinSCP).
The error message suggests that WinSCP is not parsing the date information correctly:
Unexpected directory listing line '-rw-r--r-- 1 root staff 3 25 Nov 2003 .CFUserTextEncoding'.
'2003 .' is not a valid integer value
Version of WinSCP: 3.6.1
Transfer protocol: SCP