Attachments aren't really a field. The look of the "field" is there to provide a hook for attaching files.
So, the answer is probably "no, not unless you find/write a plugin to provide a field that will do what you need"
I'm afraid not, I've never found one that met the requirements when this has come up with my clients (actually, the ones who could justify something more complex than Jira's standard attachment functionality really needed a documentation management solution, which was done externally to Jira)
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