Custom fields for attachments?

[Robert Anthony]

I have a subtask that requires 2 different files to be uploaded to it before it can be complete. Or at least that's what I want in theory. Because I want to do a bit of hand holding, I need the attachment(s) sections to be labeled so my users know what to upload in each section. Is this possible? 

[Pedro Cora]

Not by default in JIRA. 

You can check if any add-ons in Marketplace can add such functionality to JIRA. A 'hacky' way would be to add two transitions on the workflow. One for each attachment. But it seems to much of a hassle for hand holding. 

-- Pedro