i compare this problem with some encounterd with cisco equipment.
- check if there is enough space in flash.
if not you might need to delete the old image first before copying the new one.
- how did you retrieve the image, if copied by ftp, it might have been damaged (not binary).
- As explorer standard hides file-extensions
see if the file extension of the image is not "missing" (no file extension), if the file has the wrong extension it would explain why the procurve software updater states no new software available.
(and possibly also the cli and web procedures fail).
- cisco supplies different types of image.
".tar" is better suitable for upgrade using the web-interface, while the ".bin" is better for the cli (copy tftp).