If you look at the properties of the recycle bin, there may be some settings related to your situation. One is the maximum size that can be sent to the bin. Mine shows around 14000 MB, but seems to be set for the useable space in the specific partition. Since you have already check these numbers, maybe the number has been set incorrectly.
Are your recycle bins showing empty, and considering each partition has it own, is the one you are using set for enough space.
Is it just a .jpg that will not work correctly? Are there any special attributes on the files that do not work?
Edit: Oh, and your shift key isn't sticking?