Todd,
> when you create an issue you can associate a file with it.
> Unfortunately, you are not able to enter a description of the file being
> attached, as is possible when you attach a file after the creation of an
> issue.
>
> Perhaps it would be nice to be able to specify a description at the
> creation time, or edit a description of a file at a later stage.
>
Well, the description for the attachments is not available because you would
usually explain what the files are in the issue description itself.
i.e.: "I'm reproducing this bug XYZ in the software, and I'm attaching the
error logs to this report"
So I would think this feature is not really needed.
--Joao