scenario:

1. a bug gets identified by client - they create an issue
2. project manager investigates and confirms it is a bug - adds a screen shot
3. tech team discuss how to fix via comments
4. tech A draws 2 diagrams for options, adds to issue
5. tech B takes a screenshot confirming the bug exists in other areas

When someone comes to this issue, it is quite difficult to follow the conversation unless you also check the dates on each of the attachments. ie: some comments refer to the image. It can be hard to understand the attached file without the related comment.

Adding files is a bit misleading as when you attach a file you can also add a comment - but the two don't really connect in the UI (unless you view all activity). Even then it is just the name of the file rather than a thumbnail.

What would be helpful is to show a thumbnail of the image or icon of file next to the comment text. That way it would be much easier to understand the flow of discussion in comments.