As in Chap. 3 and emphasised in Chap. 4 with regard to mediated agency, the concept of dignity is central to both Stoic and neo-Stoic philosophy and specifically with regard to the problem of control, as expressed in Stoic philosophy and analogously as it applies to technology, and in particular, ICTs and AI technologies. As most of the key problems in the use of those technologies are generated through the use of AI algorithms, those problems will be analysed in conjunction with the normative impact those technologies have on well-being, on individuals and society generally. This chapter will examine and evaluate in more detail the impact of ICTs and AI technologies on well-being through a close analysis of two major problems in AI machine learning and neural network algorithms: that of the inscrutability or the black box problem and the control problem. This chapter will also suggest possible solutions to both of those problems, some of them proposed recently by AI researchers. A key concern that both those problems raise is that without transparency there is no accountability and without accountability there is no normative way to monitor AI systems for potential adverse and harmful impacts on society, let alone control them. As such, the common collective good of society and humanity generally, is at stake. This chapter will also introduce the notion of anticipatory normative controls through design to prevent or at least minimise the risk of the adverse impact of AI technologies on well-being through opacity or lack of control. Can we now like the Trojans standing on the broken walls of Troy looking down at the ruins of their fallen city hear the warnings of Cassandra “beware of Big Tech bearing gifts” before we too find the last citadel of our inner freedom and autonomy are under the control of the Big Tech companies.