Current State:

Currently the Jira work item uses the native attachment fields which doesn't support uploading the attachment with predefined labels.

 

Proposed Future State:

Jira work item can have the ability to implement app logic for attachment interaction. Users can upload attachments directly through the app using the + button (highlighted in the attached screenshot).

 

Alternative (e.g. Third Party Plugin):

App Partner has the ability to do the same in DC but is looking for the same feature in cloud.