Is it possible for the "same" file to be attached to multiple work item?
2 answers
You do not have to attach it. You can reference it in the description or comment or Summary.
Example File was attached to a "Work Item 1502" and it was given an ID 2
You can reference it in another "Work Item 1503" in the comment or description as
example adding a comment to WI
Adding it to another WorkItem