Tangible tabletop systems have been extensively proven to be able to enhance participation and engagement as well as enable many exciting activities, particularly in the education domain. However, it remains unclear as to whether students really benefit from using them for tasks that require a high level of reflection. Moreover, most existing tangible tabletops are designed as stand-alone systems or devices. Increasingly, this design assumption is no longer sufficient, especially in realistic learning settings. Due to the technological evolution in schools, multiple activities, resources, and constraints in the classroom ecosystem are now involved in the learning process. The way teachers manage technology-enhanced classrooms and the involved activities and constraints in real-time, also known as classroom orchestration, is a crucial aspect for the materialization of reflection and learning. This thesis aims to explore how educational tangible tabletop systems affect reflection, how reflection and orchestration are related, and how we can support reflection and orchestration to improve learning. It presents the design, implementation, and evaluations of three tangible tabletop systems – the DockLamp, the TinkerLamp, and the TinkerLamp 2.0 – in different learning contexts. Our experience with these systems, both inside and outside of the laboratory, results in an insightful understanding of the impacts of tangible tabletops on learning and the conditions for their effective use as well as deployment. These findings can be beneficial to the researchers and designers of learning environments using tangible tabletop and similar interfaces.