Assuming that you don't want to add metadata against the files, you can either directly copy the files to the server file system where the upload share is pointing to or you could use the drag and drop functionality. Drag and drop allows you to select some files in Windows Explorer and then drag and drop them into the File Manager location in the IE browser window. To use this function you need to enable the permission and install the client side tools.

Hi! As an alternative you can check out the WebDAVX project, it'll expose EPiServer folders as webfolders accessible over WebDAV. More information at http://r.ep.se/projects/webdavx . If youre using XP as the client and have the WebClient service started, you can even assign a driveletter to the webfolder and copy files and whole structures from a command prompt(!) Note however that the WebDAVX project is released as a technical preview and its future is not really set yet, it kinda depends on the feedback we'll get. /johan