We investigate the use of on-line contextual video assistance to improve the learnability of software functionality. After discussing motivations and design goals for such forms of assistance, we present our new technique, ToolClips. ToolClips augment traditional tooltips to provide users with quick and contextual access to both textual and video assistance. In an initial study we found that users successfully integrated ToolClip usage into the flow of their primary tasks to overcome learnability difficulties. In a second study, we found that with ToolClips, users successfully completed 7 times as many unfamiliar tasks, in comparison to using a commercial professionally developed on-line help system. Users also retained the information obtained from ToolClips, performing tasks significantly faster one week later.