This is now possible with the new list view for files, which includes the ability to reorder files attached to records.
You can use the Select files button or drag files from your computer.
We have a lot of files and its impossible to distinguish or choose the right one in the grid view, with the title truncated.
I'd also like to suggest more modern looking icons if an update is being made in this area. It's just a visual annoyance, but the current ones look to be using an icon format that is based on several Microsoft Office generations past.
It would be great to have additional metadata associated with a file, and then combine this with the proposed list view so that a meaningful grid of information is displayed for available files. It would be very helpful to be able to make these metadata fields user-definable. As the product manager I can then offer a flexible document repository with great filter capabilities.
Please implement this when attaching files to features. It would make life much easier.
This should be done similar to how Aha! handles VIEWs where they show on the toolbar the toggle icons to toggle back and forth between icon view and list view.
You won't be notified about changes to this idea.