You can add revisions to any attachment you have added to your Jira issue for version control. 

  1. Open the issue with an attachment added (i.e., named File A).
  2. Upload a new revision of the attachment to the Jira issue with the same name  (i.e., File A).
  3. See that the Smart Attachments app has automatically grouped your attachments together under the file name. The latest version will be on top of the list.

Note that attachments with different names can't be treated as file revisions.