Hi Ann,
As a Victor said, it's impossible. You have only one system field "Attachment". This problem is described also in this ticket: https://jira.atlassian.com/browse/JRASERVER-4925. Unfortunately, it was resolved with "Won't Fix" resolution :(
Maybe would you like to try Smart Attachments from StiltSoft? I know that using it you can create some categories for attachments and manage them in the easy way. It could be a workaround for your problem.
Cheers,
Kate
Ann,
You can attach many files. All will go in one place.
https://confluence.atlassian.com/servicedeskserver/attaching-files-and-screenshots-to-issues-939937192.html
Victor
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Ann,
There's no way to add an attachment field. You'd have to use the system attachment option. All you can do is drag and drop several files. All go into one bucket.
victor
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