An easy way to upload multiple files in one go is to use an add-on product for Plone supporting this. We have the choice between three of these products:
collective.uploadify, PloneFlashUpload, and
atreal.massloader. Each of these products has a different strategy on how to get the data into Plone. Two of them use Flash for posting the asynchronous data, and one uses ZIP storage for bundling the data before uploading. What they have in common is that they all use the native web GUI. Editors of the content don't have to change the client to upload binary data. All actions can be done in the web browser with the familiar GUI of Plone.
The youngest member of the bulk upload ...