Encoding data and computation in the digital form has enabled us to extend our capability to process information at rates and scales never possible before. However, the digital medium carries inherent risks and poses grand challenges. First, ensuring a long-term and reliable access to digital assets is of paramount importance. Yet, we are still grappling with the meaning of preservation in the face of tight dependences and dynamic nature of the computing ecosystem. Second, interaction of humans and technologies has been fundamentally deficient. Humans cannot consume nor act on digital directly. It requires software to mediate the interaction. Furthermore, the contemporary computing systems are complex and inaccessible to average users. At the same time, the computer interaction models are insufficient to leverage intelligent feedback of an average user. In this presentation we discuss these issues in detail and consider the approaches to address them.