The document summarizes research on developing a self-report tool called the Smiley Based Affect Indicator (SBAI) to measure user affect using smiley faces. An online survey with over 990 responses was conducted to collect empirical data on how smileys are associated with levels of valence and arousal. The results supported using SBAI as a metacognitive scaffolding tool to add affect labels to system prompts. Further analysis of the data and interface refinements were suggested to improve SBAI for measuring affect without interrupting the user experience.