Please post a log file both from GUI and script.
I have this script winscp.exe /console /script=c:\batch\rne_up.txt /log=c:\batch\winscplog.txt
option batch on
option confirm off
option transfer binary :roll:
keepuptodate d:\RNE /
On command keeptoupdate i see in console "watching for changes" and that is all
Watching for changes, press Ctrl-C to abort.
Scanning 'd:\RNE' for subdirectories...
Watching for changes in 1478 directories...
If I run synchronize from GUI, all worked ok (changes are detected after 30 seconds)
WinSCP 4.3.4 on Windows Server 2008 x64
Thank for help