When an image/attachments with the similar file name is being attached to a comment. The previous comment with inline image/attachments will be pointed to the latest updated image.
At a support/helpdesk environment, user does not have control over the mail client that the customers use. Which in most of the case, image/attachments are pasted directly to the body of the mail. Causing the default file naming to be identical.
This has seriously crippled the usability of JIRA as the old comments (with similar file name) no longer represents the state that it should be in.
To add to the pain, the incoming mail is being deleted upon creation. That removed the reference to track back and it causes confusion especially on a long running case where 4-5 inline image is added. They can only rely on the time recorded when the issue is added to reference it back.
To have the ability to configure the attachments to be appended with time stamp. There should be a toggle in project level so that user get to choose if this only applies to specific projects.
Also could consider wiki markup with a timestamp column, to place that information to point the attachment to the right one.
Frequently, we have users who upload images or project requirement Word docs to a JIRA project and when the project changes they upload an updated version of the document again. This ends up in showing the same file name twice.
1) Provide the user the ability to overwrite (update) an attachment they have already uploaded. (Even if they don't have manage attachments? Or only if they do? Not sure.)
2) When a user uploads a file with a filename that has already been uploaded, change the visible filename to myfile.gif (2) or something similar.