Hi Jess,
From your description, it sounds like you're trying to use the Drag and Drop Uploader. I wrote a short description awhile back for someone who couldn't get the drag-and-drop to work, so I'll embellish on that. Here goes....
I assume you've gotten to the Drag-and-Drop page OK using Internet Explorer (IE), and you see a title "ActiveX Image Upload" in orange at the top left and a big empty window box with column titles of Files and Size. Note, there are three bullet items describing the processes, but I'll expand here with method that I use. To active that empty Window, you need to click on it. You'll notice that your cursor changes from a HAND to the normal cursor ARROW, signifying it's Active and ready.
The drag-and-drop is done between two different windows, so you also need to bring up a window with the desktop Windows Explorer (not IE) that has the file names or pictures you want to send. You can do that using the "Select" or "Select Folder" buttons at the bottom of the page. I keep mine in WinXP file Folders with "Thumbnail" views, so I can literally see what I want to send. Then, select and drag each one (or all you want with multiple selection) and drop them in the upload Window box. You should see it populate with the file names and sizes.
Having two open windows on the same screen might be a little tight, but just size the Windows appropriate to your monitor.
When you've dragged all the files to the box that you want to upload, just select the Upload Button and a pop-up window appears to give you progress on the transfer. It might seem like it freezes at the end, but just give it (the server) a minute to digest the photos and it should give you a screen showing successful transfer(s).
Hope that helps. I and other Forum members can certainly help with questions.
Danno