The riles or intellectual property on computer systems have increasingly been exposed to such threats that they can be flowed out by internal users or outer attacks through the network. The File Outflow Monitoring System monitors file outflows at server by making the toe when users copy files on client computers into storage devices or print them, The monitoring system filters I/O Request packet by I/O Manager in kernel level if files are flowed out by copying, while it uses Win32 API hooking if printed. As a result, it has exactly made the log and monitored file outflows, which is proved through testing in Windows 2000 and XP.