Can't put files into nested folders in dock

Whenever I try to put a file into a folder I have in my dock, it will only let me put it in the first level of the folder. Ideally, I would want the folder to pop open and show the next level of folders so I can navigate through levels of nested folders to put the file in the exact place I want deep within my folder hierarchy. I know I can hold down Control on a folder in the dock to show my nested folders, but how can I drag files into those nested folders? I thought this was supposed to be automatic in Tiger. Please help.

Yes- Easy!
When you have your Creative Media Explorer open and your portable device connected, you will see your Zen V Series Media Explorer in the SOURCE window in the upper LH corner. Click on the "+" in front of the Zen V Series icon and it will display the list of folders on the device.
Right click on the main folder for the category you want to put the sub folder in and you will get a drop down menu.
Select "New folder" and you will get the "New Folder" box asking you what name you want for your new folder. It's that easy.

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