In past we have covered two free utilities Tinypicuploader & Imageshaker which lets you to upload images right form your desktop to Imageshack image sharing website. Unfortunately recent changes made to Imageshack.us have broken all the tools. If you are looking for working Imageshack uploader then here is ShakeShag open source utility.
ShackShag is a small tool allowing you to upload many images to imageshack.us hosting. ShackShag is command line utility and provides simplest way upload multiple images simultaneously.
ShackShag Imageshack Uploader