fileupload element not saving file on edit

i have a list with the fileupload element so users can attach .pdf documents only. I've given the users the ability to edit their listing including the fileupload element. When editing the entry, the attached file appears to be there but when saving it prompts to select the file again. When you do attach the file again it doesn't save the file to the entry. The entry on the front is for the file link is missing.

How do I setup the fileupload element to retain the information on editing by the user?
 
This should do.
Is this a simple fileupload element or an ajaxfied one?
Do you have validation errors on your form?
 
We are in need of some funding.
More details.

Thank you.

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