First let me thank you for your wondful product, it has already saved me tons of time.
I have been having some problems with the "Keep Remote Directory up to Date" function. At first, it did not appear to be working at all for me. Some research through the boards here have led me to change my Server offset time in SCP settings as my local client runs CST and my server runs GMT. I have "Preserve Timestamp" checked and copy files manually with the expected result, that the server timestamp matches my local one. However, if I turn on "Keep Remote..." and make a change to a local file, WinSCP (correctly) updates the remote file with the new version. However, the interface shows no MM:SS under the "Changed" column, only today's date, and only for that file. Checking with ls on the remote server shows a timestamp of "Apr 7 2005" where all other files show "Apr 7 15:01". Then, changing the local file no longer fires off a update of the remote file.
Not sure if this is a config issue on my side or a "feature" :D
Thanks again for WinSCP