Recent research on annotation interfaces provides provocative evidence that anchored, annotation-based discussion environments may lead to better conversations about a text. However, annotation interfaces raise complicated tradeoffs regarding screen real estate and positioning. It is argued that solving this screen real estate problem requires limiting the number of annotations displayed to users. In order to understand which annotations have the most learning value for students, this paper presents two complementary studies examining the effects of annotations on students performing a reading-to-write task. The first study used think-aloud protocols and a within-subjects methodology, finding that annotations appeared to provoke students to reflect more critically upon the primary text. This effect was particularly strong when students encountered pairs of annotations presenting different viewpoints on the same section of text. Student interviews suggested that annotations were most helpful when they caused the reader to consider and weigh conflicting viewpoints. The second study used a between-subjects methodology and a more naturalistic task to provide complementary evidence that annotations encourage more reflective responses to a text. This study found that students who received annotated materials both perceived themselves and were perceived by instructors as less reliant on unreflective summary strategies than students who received the same content but in a different format. These findings indicate that the learning value of an annotation lies in its ability to provoke students to consider and weigh new perspectives on the primary text. When selected effectively, annotations provide a critical scaffolding that can support students' critical thinking and argumentation activities. Collaborative digital libraries and applications for the Web 2.0 should be designed with this learning framework in mind.