Ability to update a file attachment of a feature and update in the linked record of JIRA as well

Hi - We have Aha! - Jira integration where our features are mapped to JIRA stories.  Features also have several file attachments which get propagated to JIRA stories.  However, our Product Managers need to update the file attachments. Currently there is no way to update the file attachment except to delete and attach again. When they do this, the deleted files (which are outdated) still remain in JIRA and the latest version files attached to the feature gets propagated to JIRA and added as new attachments. In JIRA story, it has both old version of file as well as new version of file which is causing confusion to the developers. 

So the requirement is as a Product Manager, I'd like to be able to update the file attachment (same name) of a feature causing update to the corresponding linked records file attachment.