This report provides an in-depth analysis of the theoretical foundations of the concepts of trust and confidence and their correlation to the notions of risk, agency and legitimacy. These theoretical underpinnings are thereafter applied to permissionless blockchains, in order to identify how the foundational nature of the technology lends itself to bridging traditional paradigms in generating greater trust and confidence amongst users. We first review the literature which distinguishes the concept of trust from confidence before turning to major scholarly contributions on interpersonal trust, system trust and trust in technology. This literature has been examined through the lens of a multi-disciplinary reading group, which subsequently brings to bear practical and philosophical considerations in the use of blockchain technology in the modern world. The report concludes by providing the key areas in which trust can be reinforced, identifies the limitations of traditional factors as a measure for building trust with a decentralised and pseudonymous environment and clearly defines the differing levels of trust and confidence which are required within an on-chain and off-chain governance structure and its nexus to engendering legitimacy.