A conceptual analysis of trust in terms of trustworthiness is set out, where trustworthiness is the property of an agent that she does what she claims she will do, and trust is an attitude taken by an agent to another, that the former believes that the latter is trustworthy. This analysis is then used to explore issues in the deployment of trustworthy digital systems online. The ideas of a series of philosophers from the Enlightenment – Hobbes, Burke, Rousseau, Hume, Smith and Kant – are examined in the light of this exploration to suggest how we might proceed in the Digital Enlightenment to ensure that systems are both trustworthy and trusted.