The Web is changing. The much vaunted Web 2.0 sees once static pages evolving into hybrid applications. Content that was once simple to surf is now becoming increasingly complicated due to the many areas of dynamic content "dotted" throughout the page. In previous studies, we have shown that unlike younger users, older users have more varied interaction patterns when using dynamic content. In addition, some older users are not aware of what to expect when interacting with dynamic content and show signs of hesitancy and uncertainty when completing tasks. In this paper, we present a tool designed to assist older uses as they use Web 2.0 content and reduce the hesitancy and frustration that was previously identified.