Videos are an increasingly popular medium for supporting learning in various educational settings. Nowadays, newly designed video-based environments contain enhanced tools that allow for specific interactions with video materials (such as adding annotations and hyperlinks) which may well support generative learning and conceptual understanding. However, to exploit the potentials of such enhanced tools, we need to gain a deeper understanding on the learning processes and outcomes that go along with using these tools. Thus, we conducted a controlled laboratory experiment with 209 participants who were engaged in learning a complex topic by using different enhanced video tools (annotations vs. hyperlinks vs. control group) in different social learning settings (individual vs. collaborative learning in dyads). Findings revealed that participants who learned with hyperlinks and participants in collaborative settings created hypervideo products of higher quality than learners in other conditions. Participants who learned with annotations assessed their knowledge gain higher and had higher results in conceptual understanding when they experienced low cognitive load. With our study we contribute new original work to advance cognitive research on learning with enhanced video learning environments. Limitations and recommendations for future research are discussed.