People can organize information items by placing them into folders or by tagging them with labels. Over the years there has been considerable discussion on the relative merits of folders vs. labels. But there is relatively little empirical data directly comparing people's experiences with each model of organization on comparable sets of information. We compared participants' experiences organizing information with both folders and labels over time. Results indicate that each model has its strengths and weaknesses when assessed with respect to basic activities of personal information management (PIM) such as keeping, organizing and re-finding. Results afford a deeper, more detailed understanding of each model in practice. This understanding is achieved by engaging participants in an active, “hands-on” comparison of models over a period of time. Study results point to syntheses in tool support for organizing information that might combine strengths of folders and labels while avoiding the inadvertent introduction of weaknesses from these models.