In recent years, educational practitioners and learning technologists have been designing, developing and deploying a wide range of innovative environments to enhance meaningful, seamless and exciting learning experiences. In these learning environments, students may interact as individuals or in groups across several learning spaces, while utilizing various technologies that support different contexts of use. However, despite these efforts and progress in this field, there are still a number of technical challenges associated with software architecture issues related to how to implement tools that support seamless learning. In this chapter, we describe our ongoing research related to the design, development and deployment of different software solutions to support seamless learning activities across a variety of settings. Here, we examine and propose a candidate software architecture that is inspired by our implementation of seamless learning activities. In particular, we direct our efforts towards enhancing and facilitating these activities by supporting the reuse and remixing of digital content generated by learners and teachers. The features of the proposed architecture also support the reusability and interoperability of software components and micro-services for different interactions. We address architectural challenges identified in activities we have carried out during the last five years. Three different use cases of seamless learning activities in different subject areas are analysed and the supporting technical and software solutions examined, in order to identify and extract the salient features and functional requirements of the proposed architecture. In addition, we use these cases to examine, analyse and propose new and refined ways to cope with challenges related to the activities that need to be implemented for seamless learning flow. We present and discuss our results describing an architecture capable of supporting meaningful, appealing and seamless learning experiences that are independent of subject matter, context of use and supporting technological solutions. © 2019, Springer Nature Singapore Pte Ltd.